Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/96340
標題: The development of novel bis-NHCs precursors as versatile ligands and their applications in catalytic reactions.
開發新型雙-含氮雜環碳烯前驅物及其在催化反應上之應用
作者: Chien-Cheng Chiu
邱建誠
關鍵字: 含氮雜環碳烯
催化
NHCs
catalysis
引用: CH1 (1) Regnault, H. V. Ann. Chim. Phys. 1839, 71, 427. (2) Dumas, J. B. Ann. Chim. Phys. 1835, 58, 28. (3) Perrot, A. Ann. 1857, 101, 375. (4) Butlerov, A. M. Ann. 1861, 120, 356. (5) Demselben Ann. Chim. Phys. 1862, 123, 121. (6) Hine, J. J. Am. Chem. Soc. 1950, 72, 2438. (7) Staudinger, H.; Kupfer, O. Ber. Deut. Chem. Ges. 1912, 45, 501. (8) Bender, C. F.; Schaefer, H. F. J. Am. Chem. Soc. 1970, 92, 4984. (9) Foster, J. M.; Boys, S. F. Rev. Mod. Phys. 1960, 32, 305. (10) Salem, L.; Rowland, C. Angew. Chem. Int. Ed. Engl. 1972, 11, 92. (11) Fischer, E. O.; Maasböl, A. Angew. Chem. Int. Ed. 1964, 3, 580. (12) Lage, M. L.; Fernandez, I.; Mancheno, M. J.; Sierra, M. A. Inorg. Chem. 2008, 47, 5253. (13) Rudler, H.; Parlier, A.; Certal, V.; Lastennet, G.; Audouin, M.; Vaissermann, J. Eur. J. Org. Chem. 2004, 2004, 2471. (14) Meca, L.; Dvořák, D.; Ludvík, J.; Císařová, I.; Štěpnička, P. Organometallics 2004, 23, 2541. (15) Barluenga, J.; Flórez, J.; Fañanás, F. J. J. Organomet. Chem. 2001, 624, 5. (16) Aumann, R. Eur. J. Org. Chem. 2000, 2000, 17. (17) Hegedus, L. S. Tetrahedron 1997, 53, 4105. (18) Aoki, S.; Fujimura, T.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 2985. (19) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98. (20) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. Int. Ed. 1995, 34, 2039. (21) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100. (22) Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746. (23) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875. (24) Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899. (25) Tschugajeff, L.; Skanawy-Grigorjewa, M.; Posnjak, A. Z. Anorg. Allg. Chem. 1925, 148, 37. (26) Burke, A.; Balch, A. L.; Enemark, J. H. J. Am. Chem. Soc. 1970, 92, 2555. (27) Rouschias, G.; Shaw, B. L. J. Chem. Soc. Chem. Commun. 1970. (28) Butler, W. M.; Enemark, J. H.; Parks, J.; Balch, A. L. Inorg. Chem. 1973, 12, 451. (29) Stork, J. R.; Olmstead, M. M.; Balch, A. L. Inorg. Chem. 2004, 43, 7508. (30) Fehlhammer, W. P.; Fritz, M. Chem. Rev. 1993, 93, 1243. (31) Wanzlick, H. W.; Schikora, E. Angew. Chem. 1960, 72, 494. (32) Wanzlick, H. W.; Kleiner, H. J. Angew. Chem. 1961, 73, 493. (33) Wanzlick, H.-W.; Schikora, E. Chem. Ber. 1961, 94, 2389. (34) Lemal, D. M.; Lovald, R. A.; Kawano, K. I. J. Am. Chem. Soc. 1964, 86, 2518. (35) Winberg, H. E.; Carnahan, J. E.; Coffman, D. D.; Brown, M. J. Am. Chem. Soc. 1965, 87, 2055. (36) Denk, M. K.; Hatano, K.; Ma, M. Tetrahedron Lett. 1999, 40, 2057. (37) Liu, Y.; Lemal, D. M. Tetrahedron Lett. 2000, 41, 599. (38) Taton, T. A.; Chen, P. Angew. Chem. Int. Ed. Engl. 1996, 35, 1011. (39) Andrew Taton, T.; Chen, P. Angew. Chem. 1996, 108, 1098. (40) Liu, Y.; Lindner, P. E.; Lemal, D. M. J. Am. Chem. Soc. 1999, 121, 10626. (41) Hahn, F. E.; Wittenbecher, L.; Le Van, D.; Fröhlich, R. Angew. Chem. Int. Ed. 2000, 39, 541. (42) Böhm, V. P. W.; Herrmann, W. A. Angew. Chem. Int. Ed. 2000, 39, 4036. (43) Kirmse, W. Angew. Chem. Int. Ed. 2010, 49, 8798. (44) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290. (45) Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361. (46) Cazin, C. S. J., Ed.; Springer Netherlands: 2011; Vol. 32, p 2. (47) Hahn, F. E.; Jahnke, M. C. Angew. Chem. Int. Ed. Engl. 2008, 47, 3122. (48) Hillier, A. C.; Sommer, W. J.; Yong, B. S.; Petersen, J. L.; Cavallo, L.; Nolan, S. P. Organometallics 2003, 22, 4322. (49) Lavallo, V.; Canac, Y.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Science 2006, 312, 722. (50) Despagnet-Ayoub, E.; Grubbs, R. H. J. Am. Chem. Soc. 2004, 126, 10198. (51) Davies, C. J.; Page, M. J.; Ellul, C. E.; Mahon, M. F.; Whittlesey, M. K. Chem. Commun. 2010, 46, 5151. (52) Dunsford, J. J.; Cavell, K. J. Organometallics 2014, 33, 2902. (53) Iwasaki, F.; Yasui, M.; Yoshida, S.; Nishiyama, H.; Shimamoto, S.; Matsumura, N. Bull. Chem. Soc. Jpn. 1996, 69, 2759. (54) Page, M. J.; Lu, W. Y.; Poulten, R. C.; Carter, E.; Algarra, A. G.; Kariuki, B. M.; Macgregor, S. A.; Mahon, M. F.; Cavell, K. J.; Murphy, D. M.; Whittlesey, M. K. Chem. Eur. J. 2013, 19, 2158. (55) Bazinet, P.; Ong, T.-G.; O'Brien, J. S.; Lavoie, N.; Bell, E.; Yap, G. P. A.; Korobkov, I.; Richeson, D. S. Organometallics 2007, 26, 2885. (56) Alder, R. W.; Blake, M. E.; Bortolotti, C.; Bufali, S.; Butts, C. P.; Linehan, E.; Oliva, J. M.; Guy Orpen, A.; Quayle, M. J. Chem. Commun. 1999, 241. (57) Collins, L. R.; Rookes, T. M.; Mahon, M. F.; Riddlestone, I. M.; Whittlesey, M. K. Organometallics 2014, 33, 5882. (58) Iglesias, M.; Beetstra, D. J.; Cavell, K. J.; Dervisi, A.; Fallis, I. A.; Kariuki, B.; Harrington, R. W.; Clegg, W.; Horton, P. N.; Coles, S. J.; Hursthouse, M. B. Eur. J. Inorg. Chem. 2010, 2010, 1604. (59) Scarborough, C. C.; Grady, M. J.; Guzei, I. A.; Gandhi, B. A.; Bunel, E. E.; Stahl, S. S. Angew. Chem. Int. Ed. Engl. 2005, 44, 5269. (60) Scarborough, C. C.; Popp, B. V.; Guzei, I. A.; Stahl, S. S. J. Organomet. Chem. 2005, 690, 6143. (61) Lu, W. Y.; Cavell, K. J.; Wixey, J. S.; Kariuki, B. Organometallics 2011, 30, 5649. (62) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39. (63) Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem. Int. Ed. Engl. 2007, 46, 2988. (64) Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev. 2015, 115, 9307. (65) Menon, R. S.; Biju, A. T.; Nair, V. Beilstein. J. Org. Chem. 2016, 12, 444. (66) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12. (67) Weskamp, T.; Kohl, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem. Int. Ed. 1999, 38, 2416. (68) Weskamp, T.; Kohl, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem. 1999, 111, 2573. (69) Flores-Figueroa, A. n.; Kaufhold, O.; Hepp, A.; Fröhlich, R.; Hahn, F. E. Organometallics 2009, 28, 6362. (70) Thomson, J. E.; Campbell, C. D.; Concellon, C.; Duguet, N.; Rix, K.; Slawin, A. M.; Smith, A. D. J. Org. Chem. 2008, 73, 2784. (71) Bielawski, C. W.; Grubbs, R. H. Angew. Chem. 2000, 39, 2903. (72) Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem. 2000, 39, 3898. (73) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674. (74) Raubenheimer, H. G.; Cronje, S.; Olivier, P. J.; Toerien, J. G.; van Rooyen, P. H. Angew. Chem. Int. Ed. Engl. 1994, 33, 672. (75) Schoffler, A. L.; Makarem, A.; Rominger, F.; Straub, B. F. Beilstein. J. Org. Chem. 2016, 12, 1566. (76) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. Int. Ed. Engl. 1995, 34, 1021. (77) Gade, L. H.; Bellemin-Laponnaz, S. Coord. Chem. Rev. 2007, 251, 718. (78) Johnson, C.; Albrecht, M. Organometallics 2017, 36, 2902. (79) Mazloomi, Z.; Pretorius, R.; Pamies, O.; Albrecht, M.; Dieguez, M. Inorg. Chem. 2017, 56, 11282. (80) Olguín, J.; Paz-Sandoval, M. Á. J. Organomet. Chem. 2017, 848, 309. (81) Aumann, R. Angew. Chem. Int. Ed. Engl. 1988, 27, 1456. (82) Caló, V.; Sole, Roberta D.; Nacci, A.; Schingaro, E.; Scordari, F. Eur. J. Org. Chem. 2000, 2000, 869. (83) Yen, S. K.; Koh, L. L.; Huynh, H. V.; Andy Hor, T. S. J. Organomet. Chem. 2009, 694, 332. (84) Nelson, D. J.; Nolan, S. P. Chem. Soc. Rev. 2013, 42, 6723. (85) Fekete, Á.; Nyulászi, L. J. Organomet. Chem. 2002, 643-644, 278. (86) Schoeller, W. W.; Eisner, D. Inorg. Chem. 2004, 43, 2585. (87) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335. (88) Chianese, A. R.; Kovacevic, A.; Zeglis, B. M.; Faller, J. W.; Crabtree, R. H. Organometallics 2004, 23, 2461. (89) Chianese, A. R.; Li, X.; Janzen, C. M.; Zeglis, B. M.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663. (90) Dorta, R.; Stevens, E. D.; Hoff, C. D.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 10490. (91) Jafarpour, L.; Nolan, S. P. J. Organomet. Chem. 2001, 617-618, 17. (92) Crabtree, R. H. J. Organomet. Chem. 2006, 37, 5451. (93) Lee, M.-T.; Hu, C.-H. Organometallics 2004, 23, 976. (94) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370. (95) Nemcsok, D.; Wichmann, K.; Frenking, G. Organometallics 2004, 23, 3640. (96) Schneider, S. K.; Roembke, P.; Julius, G. R.; Loschen, C.; Raubenheimer, H. G.; Frenking, G.; Herrmann, W. A. Eur. J. Inorg. Chem. 2005, 2005, 2973. (97) Iglesias, M.; Beetstra, D. J.; Stasch, A.; Horton, P. N.; Hursthouse, M. B.; Coles, S. J.; Cavell, K. J.; Dervisi, A.; Fallis, I. A. Organometallics 2007, 26, 4800. (98) Penka, E. F.; Schläpfer, C. W.; Atanasov, M.; Albrecht, M.; Daul, C. J. Organomet. Chem. 2007, 692, 5709. (99) Radius, U.; Bickelhaupt, F. M. Organometallics 2008, 27, 3410. (100) Radius, U.; Bickelhaupt, F. M. Coord. Chem. Rev. 2009, 253, 678. (101) Antonova, N. S.; Carbó, J. J.; Poblet, J. M. Organometallics 2009, 28, 4283. (102) Srebro, M.; Michalak, A. Inorg. Chem. 2009, 48, 5361. (103) Tonner, R.; Frenking, G. Organometallics 2009, 28, 3901. (104) Hobbs, M. G.; Knapp, C. J.; Welsh, P. T.; Borau-Garcia, J.; Ziegler, T.; Roesler, R. Chem. Eur. J. 2010, 16, 14520. (105) Yang, J.-W.; Chen, C.-S.; Dai, H.-F.; Chen, C.-H.; Yeh, W.-Y. J. Organomet. Chem. 2011, 696, 1487. (106) Credendino, R.; Falivene, L.; Cavallo, L. J. Am. Chem. Soc. 2012, 134, 8127. (107) Comas-Vives, A.; Harvey, J. N. Eur. J. Inorg. Chem. 2011, 2011, 5025. (108) Braun, M.; Frank, W.; Ganter, C. Organometallics 2012, 31, 1927. (109) Rogers, M. M.; Stahl, S. S.; Glorius, F.; Springer, Berlin, Heidelberg: 2006; Vol. 21, p 21. (110) Konnick, M. M.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 10212. (111) C. Green, J.; G. Scurr, R.; L. Arnold, P.; Geoffrey N. Cloke, F. Chem. Commun. 1997, 1963. (112) Green, J. C.; Herbert, B. J. Dalton Trans. 2005, 1214. (113) Cavallo, L.; Correa, A.; Costabile, C.; Jacobsen, H. J. Organomet. Chem. 2005, 690, 5407. (114) Hu, X.; Tang, Y.; Gantzel, P.; Meyer, K. Organometallics 2003, 22, 612. (115) Hu, X.; Castro-Rodriguez, I.; Olsen, K.; Meyer, K. Organometallics 2004, 23, 755. (116) Scott, N. M.; Dorta, R.; Stevens, E. D.; Correa, A.; Cavallo, L.; Nolan, S. P. J. Am. Chem. Soc. 2005, 127, 3516. (117) Kantchev, E. A.; O'Brien, C. J.; Organ, M. G. Angew. Chem. Int. Ed. Engl. 2007, 46, 2768. (118) Wallach, J. Ber. Dtsch. Chem. Ges. 1925, 15, 645. (119) Gridnev, A. A.; Mihaltseva, I. M. Synth. Commun. 1994, 24, 1547. (120) Furstner, A.; Alcarazo, M.; Cesar, V.; Lehmann, C. W. Chem. Commun. 2006, 2176. (121) Bon, R. S.; van Vliet, B.; Sprenkels, N. E.; Schmitz, R. F.; de Kanter, F. J.; Stevens, C. V.; Swart, M.; Bickelhaupt, F. M.; Groen, M. B.; Orru, R. V. J. Org. Chem. 2005, 70, 3542. (122) Chu, Y.; Deng, H.; Cheng, J. P. J. Org. Chem. 2007, 72, 7790. (123) Magill, A. M.; Cavell, K. J.; Yates, B. F. J. Am. Chem. Soc. 2004, 126, 8717. (124) Bordwell, F. G.; Satish, A. V. J. Am. Chem. Soc. 1991, 113, 985. (125) Oehninger, L.; Rubbiani, R.; Ott, I. Dalton Trans. 2013, 42, 3269. (126) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. 1995, 107, 1119. (127) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. Int. Ed. Engl. 1995, 34, 1021. (128) Öfele, K. J. Organomet. Chem. 1968, 12, 42. (129) Wanzlick, H. W.; Schönherr, H. J. Angew. Chem. 1968, 80, 154. (130) Wanzlick, H. W.; Schönherr, H. J. Angew. Chem. Int. Ed. Engl. 1968, 7, 141. (131) Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 2371. (132) Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Angew. Chem. 1995, 107, 2602. (133) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F.; Manojlović-Muir, L.; Muir, K. W. J. Chem. Soc. D. 1971, 0, 400. (134) Lappert, M. F. J. Organomet. Chem. 2005, 690, 5467. (135) Çetinkaya, B.; Özdemir, I.; Dixneuf, P. H. J. Organomet. Chem. 1997, 534, 153. (136) Özdemir, I.; Demir, S.; Çetinkaya, B.; Toupet, L.; Castarlenas, R.; Fischmeister, C.; Dixneuf, P. H. Eur. J. Inorg. Chem. 2007, 2007, 2862. (137) Yiğit, B.; Yiğit, M.; Özdemir, İ.; Çetinkaya, E. Transit. Metal Chem. 2012, 37, 297. (138) Ödemir, I.; Yaşar, S.; Çetinkaya, B. Transit. Metal Chem. 2014, 30, 831. (139) Gürbüz, N.; Yaşar, S.; Özcan, E. Ö.; Özdemir, İ.; Çetinkaya, B. Eur. J. Inorg. Chem. 2010, 2010, 3051. (140) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953. (141) Arduengo, A. J.; Dias, H. V. R.; Calabrese, J. C.; Davidson, F. Organometallics 1993, 12, 3405. (142) Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972. (143) Sakaguchi, S.; Yoo, K. S.; O'Neill, J.; Lee, J. H.; Stewart, T.; Jung, K. W. Angew. Chem. 2008, 120, 9466. (144) Yoo, K. S.; O'Neill, J.; Sakaguchi, S.; Giles, R.; Lee, J. H.; Jung, K. W. J. Org. Chem. 2010, 75, 95. (145) Bildstein, B.; Malaun, M.; Kopacka, H.; Wurst, K.; Mitterböck, M.; Ongania, K.-H.; Opromolla, G.; Zanello, P. Organometallics 1999, 18, 4325. (146) Nelson, D. J. Eur. J. Inorg. Chem. 2015, 2015, 2012. (147) Bo, L.; Na, Z.; Wanzhi, C. Prog. Chem. 2010, 22. (148) Zhang, D.; Zi, G. Chem. Soc. Rev. 2015, 44, 1898. (149) Rubio, R. J.; Andavan, G. T. S.; Bauer, E. B.; Hollis, T. K.; Cho, J.; Tham, F. S.; Donnadieu, B. J. Organomet. Chem. 2005, 690, 5353. (150) Kolychev, E. L.; Kronig, S.; Brandhorst, K.; Freytag, M.; Jones, P. G.; Tamm, M. J. Am. Chem. Soc. 2013, 135, 12448. (151) Igarashi, A.; Kolychev, E. L.; Tamm, M.; Nomura, K. Organometallics 2016, 35, 1778. (152) Ai, P.; Danopoulos, A. A.; Braunstein, P. Organometallics 2015, 34, 4109. (153) Oehlke, E.; Kong, S.; Arciszewski, P.; Wiebalck, S.; Abram, U. J. Am. Chem. Soc. 2012, 134, 9118. (154) Warratz, S.; Postigo, L.; Royo, B. Organometallics 2013, 32, 893. (155) Eguillor, B.; Esteruelas, M. A.; Oliván, M.; Puerta, M. Organometallics 2008, 27, 445. (156) Danopoulos, A. A.; Braunstein, P.; Stylianides, N.; Wesolek, M. Organometallics 2011, 30, 6514. (157) Albrecht, M.; Crabtree, R. H.; Mata, J.; Peris, E. Chem. Commun. 2002, 32. (158) Yamaguchi, Y.; Kashiwabara, T.; Ogata, K.; Miura, Y.; Nakamura, Y.; Kobayashi, K.; Ito, T. Chem. Commun. 2004, 2160. (159) Gründemann, S.; Kovacevic, A.; Albrecht, M.; Faller Robert, J. W.; Crabtree, H. Chem. Commun. 2001. (160) Kelly, R. A.; Scott, N. M.; Díez-González, S.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 3442. (161) Chartoire, A.; Frogneux, X.; Boreux, A.; Slawin, A. M. Z.; Nolan, S. P. Organometallics 2012, 31, 6947. (162) Liu, B.; Liu, B.; Zhou, Y.; Chen, W. Organometallics 2010, 29, 1457. (163) Liu, B.; Xia, Q.; Chen, W. Angew. Chem. Int. Ed. Engl. 2009, 48, 5513. (164) Lazreg, F.; Cordes, D. B.; Slawin, A. M. Z.; Cazin, C. S. J. Organometallics 2015, 34, 419. (165) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606. (166) Wöhler, F.; Liebig, J. Ann. Pharm. 1832, 3, 249. (167) Stetter, H.; Schreckenberg, M. Angew. Chem. Int. Ed. Engl. 1973, 12, 81. (168) Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm. Soc. Jpn. 1943, 63, 296. (169) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719. (170) Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899. (171) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Org. Chem. 2005, 70, 5725. (172) Vora, H. U.; Lathrop, S. P.; Reynolds, N. T.; Kerr, M. S.; Read de Alaniz, J.; Rovis, T. Org. Synth. 2011, 87, 350. (173) Hata, K.; Kozawa, M.; Baba, K. Chem. Pharm. Bull. 1976, 24, 1688. (174) Koyama, Y.; Yamaguchi, R.; Suzuki, K. Angew. Chem. 2008, 120, 1100. (175) Kimura, Y.; Sumiyoshi, M.; Taniguchi, M.; Baba, K. Cancer Sci. 2008, 99, 2336. (176) Comer, F. W.; Trotter, J. J. Chem. Soc. B. 1966. (177) Comer, F. W.; McCapra, F.; Qureshi, I. H.; Scott, A. I. Tetrahedron 1967, 23, 4761. (178) Feline, T. C.; Mellows, G.; Jones, R. B.; Phillips, L. J. Chem. Soc., Chem. Commun. 1974. (179) Trost, B. M.; Shuey, C. D.; DiNinno, F. J. Am. Chem. Soc. 1979, 101, 1284. CH2 (1) Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101. (2) O'Brien, C. J.; Kantchev, E. A.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chem. Eur. J. 2006, 12, 4743. (3) Meconi, G. M.; Vummaleti, S. V. C.; Luque-Urrutia, J. A.; Belanzoni, P.; Nolan, S. P.; Jacobsen, H.; Cavallo, L.; Solà, M.; Poater, A. Organometallics 2017, 36, 2088. (4) Lei, P.; Meng, G.; Ling, Y.; An, J.; Szostak, M. J. Org. Chem. 2017, 82, 6638. (5) GÜRbÜZ, N.; Karaca, E. Ö.; ÖZdemİR, İ.; ÇEtİNkaya, B. Turk. J. Chem. 2015, 39, 1115. (6) Haddad, B.; Villemin, D.; Belarbi, E.-h. Chem. Pap. 2014, 68, 656. (7) Melvin, P. R.; Hazari, N.; Beromi, M. M.; Shah, H. P.; Williams, M. J. Org. Lett. 2016, 18, 5784. (8) Gao, T. T.; Jin, A. P.; Shao, L. X. Beilstein. J. Org. Chem. 2012, 8, 1916. (9) Balinge, K. R.; Bhagat, P. R. C. R. Chim. 2017, 20, 773. (10) Taige, M. A.; Zeller, A.; Ahrens, S.; Goutal, S.; Herdtweck, E.; Strassner, T. J. Organomet. Chem. 2007, 692, 1519. (11) Chartoire, A.; Frogneux, X.; Nolan, S. P. Adv. Synth. Catal. 2012, 354, 1897. (12) Zhang, Y.; Lavigne, G.; Cesar, V. J. Org. Chem. 2015, 80, 7666. (13) Shi, S.; Szostak, M. Chem. Commun. 2017, 53, 10584. (14) Matsubara, K.; Sueyasu, T.; Esaki, M.; Kumamoto, A.; Nagao, S.; Yamamoto, H.; Koga, Y.; Kawata, S.; Matsumoto, T. Eur. J. Inorg. Chem. 2012, 2012, 3079. (15) Sun, Y.; Li, X.; Sun, H. Dalton Trans. 2014, 43, 9410. (16) Banach, L.; Gunka, P. A.; Buchowicz, W. Dalton Trans. 2016, 45, 8688. (17) Sato, Y.; Yamazaki, T. Synthesis 2008, 2008, 2830. (18) Hadei, N.; Kantchev, E. A.; O'Brien, C. J.; Organ, M. G. Org. Lett. 2005, 7, 3805. (19) Valente, C.; Belowich, M. E.; Hadei, N.; Organ, M. G. Eur. J. Org. Chem. 2010, 4343. (20) Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A.; O'Brien, C. J.; Valente, C. Chem. Eur. J. 2006, 12, 4749. (21) Ray, L.; Barman, S.; Shaikh, M. M.; Ghosh, P. Chem. Eur. J. 2008, 14, 6646. (22) Zhang, C.; Liu, J.; Xia, C. Chin. J. Catal. 2015, 36, 1387. (23) Gallop, C. W.; Chen, M. T.; Navarro, O. Org. Lett. 2014, 16, 3724. (24) Yang, J.; Li, P.; Zhang, Y.; Wang, L. Dalton Trans. 2014, 43, 7166. (25) Yang, J.; Wang, L. Dalton Trans. 2012, 41, 12031. (26) Peñafiel, I.; Pastor, I. M.; Yus, M.; Esteruelas, M. A.; Oliván, M.; Oñate, E. Eur. J. Org. Chem. 2011, 2011, 7174. (27) Peñafiel, I.; Pastor, I. M.; Yus, M. Eur. J. Org. Chem. 2013, 2013, 1479. (28) Lin, Y.-R.; Chiu, C.-C.; Chiu, H.-T.; Lee, D.-S.; Lu, T.-J. Appl. Organomet. Chem. 2017. (29) Zhang, Z.-H.; Li, T.-S.; Li, J.-J. Monatsh. Chem. 2006, 138, 89. (30) Meiries, S.; Speck, K.; Cordes, D. B.; Slawin, A. M. Z.; Nolan, S. P. Organometallics 2012, 32, 330. (31) Yang, X.; Xing, H.; Zhang, Y.; Lai, Y.; Zhang, Y.; Jiang, Y.; Ma, D. Chin. J. Chem. 2012, 30, 875. (32) Yılmaz, Ü.; Şireci, N.; Deniz, S.; Küçükbay, H. Appl. Organomet. Chem. 2010, 24, 414. (33) Demir, S.; Özdemir, I.; Çetinkaya, B. Appl. Organomet. Chem. 2006, 20, 254. (34) Seva, L.; Hwang, W.-S.; Sabiah, S. J. Mol. Catal. A: Chem. 2016, 418-419, 125. (35) Sakaguchi, S.; Yoo, K. S.; O'Neill, J.; Lee, J. H.; Stewart, T.; Jung, K. W. Angew. Chem. 2008, 120, 9466. (36) Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972. (37) Caddick, S.; Cloke, F. G. N.; Clentsmith, G. K. B.; Hitchcock, P. B.; McKerrecher, D.; Titcomb, L. R.; Williams, M. R. V. J. Organomet. Chem. 2001, 617-618, 635. (38) Chartoire, A.; Lesieur, M.; Falivene, L.; Slawin, A. M.; Cavallo, L.; Cazin, C. S.; Nolan, S. P. Chem. Eur. J. 2012, 18, 4517. (39) Herrmann, W. A.; Schwarz, J.; Gardiner, M. G. Organometallics 1999, 18, 4082. (40) Liu, Q.-X.; Zhao, L.-X.; Zhao, X.-J.; Zhao, Z.-X.; Wang, Z.-Q.; Chen, A.-H.; Wang, X.-G. J. Organomet. Chem. 2013, 731, 35. (41) Albano, V. G.; Bandini, M.; Monari, M.; Marcucci, E.; Piccinelli, F.; Umani-Ronchi, A. J. Org. Chem. 2006, 71, 6451. CH3 (1) Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651. (2) Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J. Q. Angew. Chem. Int. Ed. Engl. 2009, 48, 5094. (3) Wu, X. F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem. Int. Ed. Engl. 2010, 49, 9047. (4) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (5) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (6) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176. (7) Suzuki, A.; Yamamoto, Y. Chem. Lett. 2011, 40, 894. (8) Kotha, S.; Lahiri, K.; Kashinath, D. ChemInform 2003, 34. (9) Coleman, R. S.; Grant, E. B. J. Am. Chem. Soc. 1994, 116, 8795. (10) Rao, A. V. R.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135. (11) Hoye, T. R.; Chen, M. J. Org. Chem. 1996, 61, 7940. (12) Pu, L. Chem. Rev. 1998, 98, 2405. (13) Nicolaou, K. C.; Boddy, C. N. C.; Bräse, S.; Winssinger, N. Angew. Chem. Int. Ed. 1999, 38, 2096. (14) Williams, D. H.; Bardsley, B. Angew. Chem. Int. Ed. 1999, 38, 1172. (15) Bringmann, G.; Ochse, M.; Götz, R. J. Org. Chem. 2000, 65, 2069. (16) Baudoin, O.; Cesario, M.; Guénard, D.; Guéritte, F. J. Org. Chem. 2002, 67, 1199. (17) Wong, K.-T.; Hung, T. S.; Lin, Y.; Wu, C.-C.; Lee, G.-H.; Peng, S.-M.; Chou, C. H.; Su, Y. O. Org. Lett. 2002, 4, 513. (18) Hubbard, B. K.; Walsh, C. T. Angew. Chem. Int. Ed. Engl. 2003, 42, 730. (19) Watanabe, T.; Tanaka, Y.; Shoda, R.; Sakamoto, R.; Kamikawa, K.; Uemura, M. J. Org. Chem. 2004, 69, 4152. (20) Lipton, M. F.; Mauragis, M. A.; Maloney, M. T.; Veley, M. F.; VanderBor, D. W.; Newby, J. J.; Appell, R. B.; Daugs, E. D. Org. Process Res. Dev. 2003, 7, 385. (21) Martin, R.; Buchwald, S. L. Acc Chem Res 2008, 41, 1461. (22) Busch, M.; Wodrich, M. D.; Corminboeuf, C. ACS Catal. 2017, 7, 5643. (23) Caddick, S.; Cloke, F. G. N.; Hitchcock, P. B.; Leonard, J.; Lewis, A. K. d. K.; McKerrecher, D.; Titcomb, L. R. Organometallics 2002, 21, 4318. (24) Portnoy, M.; Ben-David, Y.; Rousso, I.; Milstein, D. Organometallics 1994, 13, 3465. (25) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550. (26) Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M.; Donnadieu, B. Organometallics 2003, 22, 4490. (27) DeVasher, R. B.; Moore, L. R.; Shaughnessy, K. H. J. Org. Chem. 2004, 69, 7919. (28) Iwasawa, T.; Komano, T.; Tajima, A.; Tokunaga, M.; Obora, Y.; Fujihara, T.; Tsuji, Y. Organometallics 2006, 25, 4665. (29) Ebran, J. P.; Hansen, A. L.; Gogsig, T. M.; Skrydstrup, T. J. Am. Chem. Soc. 2007, 129, 6931. (30) Dai, W. M.; Li, Y.; Zhang, Y.; Yue, C.; Wu, J. Chemistry 2008, 14, 5538. (31) Akba, O.; Durap, F.; Aydemir, M.; Baysal, A.; Gümgüm, B.; Özkar, S. J. Organomet. Chem. 2009, 694, 731. (32) Aydemir, M.; Baysal, A.; Öztürk, G. e.; Gümgüm, B. Appl. Organomet. Chem. 2009, 23, 108. (33) Doherty, S.; Knight, J. G.; McGrady, J. P.; Ferguson, A. M.; Ward, N. A. B.; Harrington, R. W.; Clegg, W. Adv. Synth. Catal. 2010, 352, 201. (34) Wong, P. Y.; Chow, W. K.; Chung, K. H.; So, C. M.; Lau, C. P.; Kwong, F. Y. Chem Commun (Camb) 2011, 47, 8328. (35) Magill, A. M.; McGuinness, D. S.; Cavell, K. J.; Britovsek, G. J. P.; Gibson, V. C.; White, A. J. P.; Williams, D. J.; White, A. H.; Skelton, B. W. J. Organomet. Chem. 2001, 617-618, 546. (36) Liu, Q.-X.; Zhao, L.-X.; Zhao, X.-J.; Zhao, Z.-X.; Wang, Z.-Q.; Chen, A.-H.; Wang, X.-G. J. Organomet. Chem. 2013, 731, 35. (37) Yılmaz, Ü.; Şireci, N.; Deniz, S.; Küçükbay, H. Appl. Organomet. Chem. 2010, n/a. (38) Demir, S.; Özdemir, I.; Çetinkaya, B. Appl. Organomet. Chem. 2006, 20, 254. (39) Seva, L.; Hwang, W.-S.; Sabiah, S. J. Mol. Catal. A: Chem. 2016, 418-419, 125. (40) Charbonneau, M.; Addoumieh, G.; Oguadinma, P.; Schmitzer, A. R. Organometallics 2014, 33, 6544. (41) Lin, Y.-R.; Chiu, C.-C.; Chiu, H.-T.; Lee, D.-S.; Lu, T.-J. Appl. Organomet. Chem. 2018, 32. (42) Shekhar, S.; Ryberg, P.; Hartwig, J. F.; Mathew, J. S.; Blackmond, D. G.; Strieter, E. R.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 3584. (43) Dyson, P. J.; Jessop, P. G. Catal. Sci. Technol. 2016, 6, 3302. CH4 (1) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581. (2) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320. (3) Mori, K.; Mizoroki, T.; Ozaki, A. Bull. Chem. Soc. Jpn. 1973, 46, 1505. (4) Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133. (5) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083. (6) Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651. (7) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. Engl. 2005, 44, 4442. (8) Maddaford, S. P.; Andersen, N. G.; Cristofoli, W. A.; Keay, B. A. J. Am. Chem. Soc. 1996, 118, 10766. (9) Fox, M. E.; Li, C.; Marino, J. P.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 5467. (10) Overman, L. E.; Rosen, M. D. Angew. Chem. Int. Ed. 2000, 39, 4596. (11) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (12) Cabri, W.; Candiani, I. Acc. Chem. Res. 2002, 28, 2. (13) Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev. 2011, 40, 5151. (14) Yang, C.; Nolan, S. P. Synlett 2001, 2001, 1539. (15) Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511. (16) Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 2371. (17) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217. (18) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215. (19) Overman, L. E.; Poon, D. J. Angew. Chem. Int. Ed. Engl. 1997, 36, 518. (20) Shaw, B. L. Chem. Commun. 1998, 1863. (21) In The Mizoroki–Heck Reaction; 1 ed.; Oestreich, M., Ed.; John Wiley & Sons, p 4. (22) Fitton, P.; Rick, E. A. J. Organomet. Chem. 1971, 28, 287. (23) Coulson, D. R. Chem. Commun. (London) 1968. (24) Fitton, P.; Johnson, M. P.; McKeon, J. E. Chem. Commun. (London) 1968. (25) Allolio, C.; Strassner, T. J. Org. Chem. 2014, 79, 12096. (26) Menezes da Silva, V. H.; Braga, A. A. C.; Cundari, T. R. Organometallics 2016, 35, 3170. (27) Ahrens, S.; Zeller, A.; Taige, M.; Strassner, T. Organometallics 2006, 25, 5409. (28) Taige, M. A.; Zeller, A.; Ahrens, S.; Goutal, S.; Herdtweck, E.; Strassner, T. J. Organomet. Chem. 2007, 692, 1519. (29) Peris, E.; Mata, J.; Loch, J. A.; Crabtree, R. H. Chem. Commun. 2001, 201. (30) Pytkowicz, J.; Roland, S.; Mangeney, P.; Meyer, G.; Jutand, A. J. Organomet. Chem. 2003, 678, 166. (31) Albert, K.; Gisdakis, P.; Rösch, N. Organometallics 1998, 17, 1608. (32) Wang, A.-E.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. Tetrahedron 2005, 61, 259. (33) Pereira, R.; Cvengroš, J. Eur. J. Org. Chem. 2013, 2013, 4233. (34) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem. Int. Ed. Engl. 2002, 41, 4746. (35) Özdemir, I.; Demir, S.; Şahin, O.; Büyükgüngör, O.; Çetinkaya, B. J. Organomet. Chem. 2010, 695, 1555. (36) Caddick, S.; Cloke, F. G. N.; Clentsmith, G. K. B.; Hitchcock, P. B.; McKerrecher, D.; Titcomb, L. R.; Williams, M. R. V. J. Organomet. Chem. 2001, 617-618, 635. (37) Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 15914. (38) Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. Angew. Chem. Int. Ed. Engl. 2003, 42, 3690. (39) O'Brien, C. J.; Kantchev, E. A.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chemistry 2006, 12, 4743. (40) Slamani, A.; Demir, S.; Özdemir, İ. Catal. Commun. 2012, 29, 141. (41) Zhang, X.; Xi, Z.; Liu, A.; Chen, W. Organometallics 2008, 27, 4401. (42) Xu, Y.; Zhang, Z.; Zheng, J.; Du, Q.; Li, Y. Appl. Organomet. Chem. 2013, 27, 13. (43) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031. (44) Lee, J.-Y.; Cheng, P.-Y.; Tsai, Y.-H.; Lin, G.-R.; Liu, S.-P.; Sie, M.-H.; Lee, H. M. Organometallics 2010, 29, 3901. (45) Hahn, F. E.; Jahnke, M. C.; Pape, T. Organometallics 2006, 25, 5927. (46) Teng, Q.; Upmann, D.; Ng Wijaya, S. A. Z.; Huynh, H. V. Organometallics 2014, 33, 3373. CH5 (1) Jones, R. S. G. Prog. Neurobiol. 1982, 19, 117. (2) Slominski, A.; Semak, I.; Pisarchik, A.; Sweatman, T.; Szczesniewski, A.; Wortsman, J. FEBS Lett. 2002, 511, 102. (3) Hardeland, R.; Pandi-Perumal, S. R.; Cardinali, D. P. Int. J. Biochem. Cell Biol. 2006, 38, 313. (4) Altun, A.; Ugur-Altun, B. Int. J. Clin. Pract. 2007, 61, 835. (5) Weissberg, J. B.; Son, Y. H.; Papac, R. J.; Sasaki, C.; Fischer, D. B.; Lawrence, R.; Rockwell, S.; Sartorelli, A. C.; Fischer, J. J. Int. J. Radiat. Oncol. Biol. Phys. 1989, 17, 3. (6) Preskorn, S. H. J. Psychiatr. Pract. 2007, 13, 253. (7) Shamon, S. D.; Perez, M. I. Cochrane Database Syst. Rev. 2009, CD007655. (8) Ballantyne, C. M.; Riegger, G.; Moore, N.; Saia, F.; Serruys, P. W. Cardiovasc. Drugs Ther. 2004, 18, 67. (9) Plosker, G. L.; Wagstaff, A. J. Drugs 1996, 51, 433. (10) Derry, C. J.; Derry, S.; Moore, R. A. Cochrane Database Syst. Rev. 2014, CD009108. (11) N. Engl. J. Med. 1991, 325, 316. (12) Palmieri, A.; Petrini, M.; Shaikh, R. R. Org. Biomol. Chem. 2010, 8, 1259. (13) Luzzio, F. A. Tetrahedron 2001, 57, 915. (14) Bartoli, G.; Bencivenni, G.; Dalpozzo, R. Chem. Soc. Rev. 2010, 39, 4449. (15) Sui, Y.; Liu, L.; Wang, D.; Chen, Y.-J. Chin. J. Chem. 2007, 25, 977. (16) Lancianesi, S.; Palmieri, A.; Petrini, M. Chem. Rev. 2014, 114, 7108. (17) Arai, T.; Sato, T. Synlett 2014, 25, 349. (18) Jørgensen, K. A. Synthesis 2003, 2003, 1117. (19) Terrasson, V.; Marcia de Figueiredo, R.; Campagne, J. M. Eur. J. Org. Chem. 2010, 2010, 2635. (20) Sheng, Y.-F.; Zhang, A. J.; Zheng, X.-J.; You, S.-L. Chin. J. Org. Chem. 2008, 28, 605. (21) Poulsen, T. B.; Jorgensen, K. A. Chem. Rev. 2008, 108, 2903. (22) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem. Int. Ed. Engl. 2004, 43, 550. (23) You, S. L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190. (24) Marques-Lopez, E.; Diez-Martinez, A.; Merino, P.; Herrera, R. Curr. Org. Chem. 2009, 13, 1585. (25) Umani-Ronchi, A.; Bandini, M.; Melloni, A.; Tommasi, S. Synlett 2005, 2005, 1199. (26) Kang, Y. K.; Kwon, B. K.; Mang, J. Y.; Kim, D. Y. Tetrahedron Lett. 2011, 52, 3247. (27) Wang, Y. Q.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156. (28) Kitanosono, T.; Miyo, M.; Kobayashi, S. Tetrahedron 2015, 71, 7739. (29) Cravotto, G.; Demartin, F.; Palmisano, G.; Penoni, A.; Radice, T.; Tollari, S. J. Organomet. Chem. 2005, 690, 2017. (30) So, C. M.; Zhou, Z.; Lau, C. P.; Kwong, F. Y. Angew. Chem. Int. Ed. Engl. 2008, 47, 6402. (31) Onitsuka, K.; Yamamoto, M.; Suzuki, S.; Takahashi, S. Organometallics 2002, 21, 581. (32) Li, Y.; Wang, W.-H.; He, K.-H.; Shi, Z.-J. Organometallics 2012, 31, 4397. (33) Schwalm, C. S.; Ceschi, M. A.; Russowsky, D. J. Braz. Chem. Soc. 2011, 22, 623. (34) Meshram, H. M.; Kumar, D. A.; Reddy, B. C. Helv. Chim. Acta 2009, 92, 1002. (35) Ji, X.; Tong, H.; Yuan, Y. Synth. Commun. 2011, 41, 372. (36) Manabe, K.; Aoyama, N.; Kobayashi, S. Adv. Synth. Catal. 2001, 343, 174. (37) Kantam, M. L.; Laha, S.; Yadav, J.; Srinivas, P. Synth. Commun. 2009, 39, 4100. (38) Liang, L.; Liu, Q.; Zhang, J.; Wang, F.; Yuan, Y. Res. Chem. Intermed. 2012, 39, 1957. (39) Bandini, M.; Melchiorre, P.; Melloni, A.; Umani-Ronchi, A. Synthesis 2002, 2002, 1110. (40) Alam, M. M.; Varala, R.; Adapa, S. R. Tetrahedron Lett. 2003, 44, 5115. (41) Xie, J.; Zhu, X.; Huang, M.; Meng, F.; Wang, M.; Wan, Y. Synth. Commun. 2010, 40, 3259. (42) Huang, G.; Sun, H.; Qiu, X.; Shen, Y.; Jiang, J.; Wang, L. J. Organomet. Chem. 2011, 696, 2949. (43) Liu, Z.; Zhang, T.; Shi, M. Organometallics 2008, 27, 2668. (44) Liu, Z.; Shi, M. Tetrahedron: Asymmetry 2009, 20, 119. (45) Drabina, P.; Brož, B.; Padělková, Z.; Sedlák, M. J. Organomet. Chem. 2011, 696, 971. (46) Gavin, D. P.; Stephens, J. C. Arkivoc 2011, 2011, 407. (47) Jiang, H.; Zhang, J.; Xie, J.; Liu, P.; Xue, M. Synth. Commun. 2016, 47, 211. (48) Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972. (49) Cheng, Y.; Lu, X.-Y.; Xu, H.-J.; Li, Y.-Z.; Chen, X.-T.; Xue, Z.-L. Inorg. Chim. Acta 2010, 363, 430. (50) Sakaguchi, S.; Yoo, K. S.; O'Neill, J.; Lee, J. H.; Stewart, T.; Jung, K. W. Angew. Chem. Int. Ed. 2008, 120, 9466. (51) Liu, B.; Xia, Q.; Chen, W. Angew. Chem. Int. Ed. Engl. 2009, 48, 5513. (52) Xiao, X.-Q.; Jin, G.-X. J. Organomet. Chem. 2008, 693, 3363. (53) Lin, J. C.; Huang, R. T.; Lee, C. S.; Bhattacharyya, A.; Hwang, W. S.; Lin, I. J. Chem. Rev. 2009, 109, 3561. (54) Corberán, R.; Ramírez, J.; Poyatos, M.; Peris, E.; Fernández, E. Tetrahedron: Asymmetry 2006, 17, 1759. (55) Wang, D.; Zhang, B.; He, C.; Wu, P.; Duan, C. Chem Commun (Camb) 2010, 46, 4728. (56) Wang, Z.; Wen, J.; Bi, Q.-W.; Xu, X.-Q.; Shen, Z.-Q.; Li, X.-X.; Chen, Z. Tetrahedron Lett. 2014, 55, 2969. (57) Liu, Y. F.; Wang, Z.; Shi, J. W.; Chen, B. L.; Zhao, Z. G.; Chen, Z. J. Org. Chem. 2015, 80, 12733. (58) Han, L.; Xing, P.; Jiang, B. Org Lett 2014, 16, 3428. (59) Kankala, S.; Pagadala, R.; Maddila, S.; Vasam, C. S.; Jonnalagadda, S. B. RSC Adv. 2015, 5, 105446. (60) Li, S.; Sun, J.; Zhang, Z.; Xie, R.; Fang, X.; Zhou, M. Dalton Trans. 2016, 45, 10577. CH6 (1) Kluwer, A. M.; Elsevier, C. J. In Handbook for Homogeneous Hydrogenation; 1st ed.; Vries, J. G. d., Elsevier, C. J., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: 2007; Vol. 1, p 375 (2) Nerozzi, F. Platin. Met. Rev. 2012, 56, 236. (3) Noyori, R.; Ohkuma, T. Angew. Chem. Int. Ed. 2001, 40, 40. (4) Enev, V.; Ewers, C. L. J.; Harre, M.; Nickisch, K.; Mohr, J. T. J. Org. Chem. 1997, 62, 7092. (5) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc., Chem. Commun. 1972. (6) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539. (7) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480. (8) Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (9) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290. (10) Zhao, D.; Candish, L.; Paul, D.; Glorius, F. ACS Catal. 2016, 6, 5978. (11) Dragutan, V.; Dragutan, I.; Demonceau, A. Platin. Met. Rev. 2005, 49, 183. (12) Ito, J.-i.; Sugino, K.; Matsushima, S.; Sakaguchi, H.; Iwata, H.; Ishihara, T.; Nishiyama, H. Organometallics 2016, 35, 1885. (13) Lee, H. M.; Smith, D. C.; He, Z.; Stevens, E. D.; Yi, C. S.; Nolan, S. P. Organometallics 2001, 20, 794. (14) Gu, P.; Zhang, J.; Xu, Q.; Shi, M. Dalton Trans 2013, 42, 13599. (15) Luo, J.; Theron, R.; Sewell, L. J.; Hooper, T. N.; Weller, A. S.; Oliver, A. G.; McIndoe, J. S. Organometallics 2015, 34, 3021. (16) Tellers, D. M.; Bergman, R. G. Organometallics 2001, 20, 4819. (17) Kerr, W. J.; Mudd, R. J.; Brown, J. A. Chemistry 2016, 22, 4738. (18) McGuinness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 1999, 18, 1596. (19) Arnold, P. L.; Cloke, F. G. N.; Geldbach, T.; Hitchcock, P. B. Organometallics 1999, 18, 3228. (20) Hauwert, P.; Boerleider, R.; Warsink, S.; Weigand, J. J.; Elsevier, C. J. J. Am. Chem. Soc. 2010, 132, 16900. (21) Jurcik, V.; Nolan, S. P.; Cazin, C. S. Chemistry 2009, 15, 2509. (22) Heckenroth, M.; Khlebnikov, V.; Neels, A.; Schurtenberger, P.; Albrecht, M. ChemCatChem 2011, 3, 167. (23) Molnár, Á.; Sárkány, A.; Varga, M. J. Mol. Catal. A: Chem. 2001, 173, 185.
摘要: N-Heterocyclic carbenes (NHCs) have emerged as new promising ligand for transition metal-mediated reactions. The use of NHC complexes in many reactions is an important field for catalysis. This dissertation is thus focused on the development of novel bis-NHCs ligands and their applications in catalytic reactions. The synthesis of bis-NHCs precursor salts and their corresponding transition metal complexes have been accomplished. The structures of ligand and metal-complexes were confirmed by X-Ray diffraction. The applications of the bis-NHCs precursor in combination with transition metal(s) to catalyze the reactions were investigated. In Suzuki-Miyaura coupling reaction, the catalytic system Pd/113c exhibited high activity toward a wide range of aryl bromides bearing different functional groups at rt. Sterically hindered di-ortho-substituted biaryls can be produced in up to 99% yields. A turnover of 200,000 have been achieved under 0.00005 mol% of Pd loading at rt. In Mizoroki-Heck coupling reaction, the catalytic system Pd/113c showed high efficacy with low catalyst loading under mild reaction conditions. The reaction proceeded smoothly with a wide variety of coupling partners at 60 °C without the addition of additive or co-catalyst. High tolerance of different functional groups in the catalytic reaction were also observed. In Friedel-Crafts alkylation reaction, the catalysis underwent smoothly at rt by generating the bis- NHCs-Pd from 113c-Ag in situ. The Friedel-Crafts adducts were obtained from different substituted nitroalkenes and different substituted indoles in up to 98% yields. Using the bis-NHCs-Ag complex 113c-Ag to catalyze the FriedelCrafts reaction directly is the first example to date. In catalytic hydrogenation, the bis-NHCs-Pd exhibited high reactivity toward different substrates to afford the reduced products in excellent yields. High compatibility toward various functional groups during the reduction process was observed. The H2 generated in situ is more atom-economic and free of the other byproduct issues. This research presents the synthesis of bis-NHCs ligand precursors in simple reactions. With the ease of generating bis-NHCs-Pd complex in situ, a highly efficient catalytic system toward various types of reactions is generated. The catalytic system shows high efficacy toward multiple catalytic reactions in low loading and mild conditions which is of great importance for both academic and industrial interests.
近年來,含氮雜環碳烯(NHCs)作為配體應用於過渡金屬催化反應已有長足發展,為了得到更高效率之催化系統,研究新型配體具有顯著之重要性。以往合成含氮雜環碳烯前驅物及其過渡金屬錯合物須使用較長合成步驟、嚴苛反應條件,限制了其大量製備的可能。因此本論文著重於發展新型高效雙含氮雜環碳烯前驅物及其於催化反應上之應用。 本研究成功地合成一系列新型雙含氮雜環碳烯前驅物及其過渡金屬錯合物,其特色為反應步驟簡短、操作方便、收率高,且配體及其錯合物均為空氣、水氣、光、熱穩定之化合物。藉由 X 光單晶繞射實驗,得以獲得配體及其金屬錯合物之固態資訊。 在鈴木-宮浦偶聯反應上,藉由使用鈀/配體 113c 衍生之催化系統,在室溫條件下對於許多不同反應物展現出優異的催化活。立體障礙高之雙鄰位取代之聯苯化合物在室溫反應條件下最高產率可達 99%。在 0.00005 mol% 之催化劑負載量下,其轉換數(turnover number, TON)在室溫下最高可達 200,000。 在溝呂木-赫克偶聯反應上,使用鈀/配體 113c 衍生之催化系統於溫和反應條件及低催化劑負載量下,有極高的催化效率。在沒有額外之添加劑或共催化劑的反應條件下,鈀/配體113c 催化系統對於多樣之偶聯起始物,可成功地反應生成偶聯產物。且反應過程中此催化系統可容忍多種不同的官能基。 藉由使用雙碳烯銀錯合物原位生成(in situ)雙碳烯鈀錯合物,在室溫下進行傅里德-克拉夫茨烷基化反應,其加成產物可由多種硝基烯烴與多樣吲哚為反應基質順利製備,產率最高可達到 98%。此外,使用雙碳烯銀錯合物作為催化劑應用於傅里德-克拉夫茨反應,為至今已知的第一個報導成功例。 於氫化反應之應用上,原位生成之雙碳烯鈀錯合物對於具有不同官能基的還原基質展現了高度相容性及化學選擇性,並且以優異的產率得到其對應還原產物。使用原位生成的氫氣應用於氫化反應上更具有原子經濟性的概念,且免除產生其他副產物的問題。 本研究完成以簡易反應製備出雙含氮雜環碳烯前驅物之方法。藉由簡單原位生成法,於反應中製備雙碳烯鈀錯合物,可得到對多樣反應皆有高反應性的催化系統。在低催化劑負載量且溫和條件下,已證明具有催化多種不同反應之能力。此一高反應性與高廣用度之催化系統,對於學術界以及工業應用上皆有相當之應用性。更多不同的催化應用正同時發展中。
URI: http://hdl.handle.net/11455/96340
文章公開時間: 2021-02-07
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