Chinese Journal of Organic Chemistry >
Boron-Based Lewis Acid Transition Metal Complexes as Potential Bifunctional Catalysts
Received date: 2017-03-01
Revised date: 2017-05-27
Online published: 2017-07-14
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21673301, 21473261, 21502023) and the Guangdong Natural Science Funds for Distinguished Young Scholar (No. 2015A030306027).
Lewis acid-transition metal (LA-TM) complexes, with the LA site functions as an electron acceptor and the TM center functions as an electron donor, have been emerging as a new type of bifunctional catalysts lately, different from traditional transition metal bifunctional catalysts. Due to their rapid developments recently, the boron-based LA-TM complexes, which are divided into three major types, the sp3, sp2, and sp boron-based complexes, are reviewed in this paper according to their binding features. Reactions promoted by this new type of LA-TM bifunctional catalysts have been surveyed, including migration reactions, activation of H-H/E-H/E-E bonds, hydrogenations, hydrosilylations, and transfer dehydrogenation reactions etc. This overview of boron-based LA-TM complexes could provide valuable information to explore the new horizon in LA-TM bifunctional catalysis.
Key words： Lewis acid; transition metal; bifunctional catalysis; boron; activation; hydrogenation; dehydrogenation
Li Yinwu , Zhang Jianyu , Shu Siwei , Shao Youxiang , Liu Yan , Ke Zhuofeng . Boron-Based Lewis Acid Transition Metal Complexes as Potential Bifunctional Catalysts[J]. Chinese Journal of Organic Chemistry, 2017 , 37(9) : 2187 -2202 . DOI: 10.6023/cjoc201703002
[1] (a) Hu, X. L. Chem. Sci. 2011, 2, 1867.
(b) Khusnutdinova, J. R.; Milstein, D. Angew. Chem., Int. Ed. 2015, 54, 12236.
[2] (a) Kubas, G. J. Chem. Rev. 2007, 107, 4152. 10, 701.
[3] (a) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300.
(b) Kuwata, S.; Ikariya, T. Chem. Commun. 2014, 50, 14290.
[4] (a) Szostak, J. W. Medicina-Buenos Aires 2016, 76, 199.
(b) Szostak, J. W. Nature 2009, 459, 171.
(c) Szostak, J. W.; Bartel, D. P.; Luisi, P. L. Nature 2001, 409, 387.
(d) Mansy, S. S.; Szostak, J. W. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 13351.
[5] (a) Fontecilla-Camps, J. C.; Volbeda, A.; Cavazza, C.; Nicolet, Y. Chem. Rev. 2007, 107, 4273.
(b) Silakov, A.; Wenk, B.; Reijerse, E.; Lubitz, W. Phys. Chem. Chem. Phys. 2009, 11, 6592.
(c) Barton, B. E.; Olsen, M. T.; Rauchfuss, T. B. J. Am. Chem. Soc. 2008, 130, 16834.
(d) Gordon, J. C.; Kubas, G. J. Organometallics 2010, 29, 4682.
[6] (a) Hou, C.; Jiang, J. X.; Li, Y. W.; Zhao, C. Y.; Ke, Z. F. ACS Catal. 2017, 7, 786.
(b) Hou, C.; Zhang, Z. H.; Zhao, C. Y.; Ke, Z. F. Inorg. Chem. 2016, 55, 6539.
[7] Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
[8] (a) Morris, R. H. Chem. Rec. 2016, 16, 2644.
(b) Annibale, V. T.; Song, D. T. RSC Adv. 2013, 3, 11432.
(c) Zhao, B. G.; Han, Z. B.; Ding, K. L. Angew. Chem., Int. Ed. 2013, 52, 4744.
(d) DuBois, D. L. Inorg. Chem. 2014, 53, 3935.
(e) Crabtree, R. H. New J. Chem. 2011, 35, 18.
(f) Appel, A. M.; Bercaw, J. E.; Bocarsly, A. B.; Dobbek, H.; DuBois, D. L.; Dupuis, M.; Ferry, J. G.; Fujita, E.; Hille, R.; Kenis, P. J. A.; Kerfeld, C. A.; Morris, R. H.; Peden, C. H. F.; Portis, A. R.; Ragsdale, S. W.; Rauchfuss, T. B.; Reek, J. N. H.; Seefeldt, L. C.; Thauer, R. K.; Waldrop, G. L. Chem. Rev. 2013, 113, 6621.
(g) Fujita, E.; Muckerman, J. T.; Himeda, Y. Biochim. Biophys. Acta, Bioenerg. 2013, 1827, 1031.
[9] (a) Owen, G. R. Chem. Commun. 2016, 52, 10712.
(b) Bouhadir, G.; Bourissou, D. Chem. Soc. Rev. 2016, 45, 1065.
(c) Dang, L.; Lin, Z.; Marder, T. B. Chem. Commun. 2009, 3987.
(d) Braunschweig, H.; Dewhurst, R. D.; Schneider, A. Chem. Rev. 2010, 110, 3924.
(e) Braunschweig, H.; Colling, M. Coord. Chem. Rev. 2001, 223, 1.
[10] (a) Devillard, M.; Bouhadir, G.; Bourissou, D. Angew. Chem., Int. Ed. 2015, 54, 730.
(b) Li, Y. W.; Hou, C.; Jiang, J. X.; Zhang, Z. H.; Zhao, C. Y.; Page, A. J.; Ke, Z. F. ACS Catal. 2016, 6, 1655.
[11] (a) Tsoureas, N.; Hamilton, A.; Haddow, M. F.; Harvey, J. N.; Orpen, A. G.; Owen, G. R. Organometallics 2013, 32, 2840.
(b) Harman, W. H.; Lin, T. P.; Peters, J. C. Angew. Chem., Int. Ed. 2014, 53, 1081.
(c) Zeng, G.; Sakaki, S. Inorg. Chem. 2013, 52, 2844.
[12] (a) Harman, W. H.; Peters, J. C. J. Am. Chem. Soc. 2012, 134, 5080.
(b) Fong, H.; Moret, M. E.; Lee, Y.; Peters, J. C. Organometallics 2013, 32, 305.
(c) Lin, T. P.; Peters, J. C. J. Am. Chem. Soc. 2013, 135, 15310.
[13] Rudd, P. A.; Liu, S. S.; Gagliardi, L.; Young, V. G.; Lu, C. C. J. Am. Chem. Soc. 2011, 133, 20724.
[14] Cammarota, R. C.; Lu, C. C. J. Am. Chem. Soc. 2015, 137, 12486.
[15] Riddlestone, I. M.; Rajabi, N. A.; Lowe, J. P.; Mahon, M. F.; Macgregor, S. A.; Whittlesey, M. K. J. Am. Chem. Soc. 2016, 138, 11081.
[16] Yang, H. F.; Gabbai, F. P. J. Am. Chem. Soc. 2015, 137, 13425.
[17] Hill, A. F.; Owen, G. R.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. 1999, 38, 2759.
[18] Tsoureas, N.; Kuo, Y. Y.; Haddow, M. F.; Owen, G. R. Chem. Commun. 2011, 47, 484.
[19] (a) Blagg, R. J.; Charmant, J. P. H.; Connelly, N. G.; Haddow, M. F.; Orpen, A. G. Chem. Commun. 2006, 2350.
(b) Landry, V. K.; Melnick, J. G.; Buccella, D.; Pang, K. L.; Ulichny, J. C.; Parkin, G. Inorg. Chem. 2006, 45, 2588.
(c) Senda, S.; Ohki, Y.; Hirayama, T.; Toda, D.; Chen, J. L.; Matsumoto, T.; Kawaguchi, H.; Tatsumi, K. Inorg. Chem. 2006, 45, 9914.
(d) Crossley, I. R.; Foreman, M. R. S. J.; Hill, A. F.; Owen, G. R.; White, A. J. P.; Williams, D. J.; Willis, A. C. Organometallics 2008, 27, 381.
(e) Crossley, I. R.; Hill, A. F. Dalton Trans. 2008, 201.
(f) Crossley, I. R.; Hill, A. F.; Willis, A. C. Organometallics 2008, 27, 312.
(g) Pang, K. L.; Tanski, J. M.; Parkin, G. Chem. Commun. 2008, 1008.
(h) Blagg, R. J.; Adams, C. J.; Charmant, J. P. H.; Connelly, N. G.; Haddow, M. F.; Hamilton, A.; Knight, J.; Orpen, A. G.; Ridgway, B. M. Dalton Trans. 2009, 8724.
(i) Rudolf, G. C.; Hamilton, A.; Orpen, A. G.; Owen, G. R. Chem. Commun. 2009, 553.
(j) Crossley, I. R.; Hill, A. F.; Willis, A. C. Organometallics 2010, 29, 326.
(k) Lopez-Gomez, M. J.; Connelly, N. G.; Haddow, M. F.; Hamilton, A.; Orpen, A. G. Dalton Trans. 2010, 39, 5221.
[20] (a) Tsoureas, N.; Bevis, T.; Butts, C. P.; Hamilton, A.; Owen, G. R. Organometallics 2009, 28, 5222.
(b) Tsoureas, N.; Haddow, M. F.; Hamilton, A.; Owen, G. R. Chem. Commun. 2009, 2538.
(c) Blagg, R. J.; Connelly, N. G.; Haddow, M. F.; Hamilton, A.; Lusi, M.; Orpen, A. G.; Ridgway, B. M. Dalton Trans. 2010, 39, 11616.
[21] Lopez-Gomez, M. J.; Connelly, N. G.; Haddow, M. F.; Hamilton, A.; Lusi, M.; Baisch, U.; Orpen, A. G. Dalton Trans. 2011, 40, 4647.
[22] Figueroa, J. S.; Melnick, J. G.; Parkin, G. Inorg. Chem. 2006, 45, 7056.
[23] Mihalcik, D. J.; White, J. L.; Tanski, J. M.; Zakharov, L. N.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L.; Rabinovich, D. Dalton Trans. 2004, 1626.
[24] Crossley, I. R.; Foreman, M. R. S.; Hill, A. F.; White, A. J. P.; Williams, D. J. Chem. Commun. 2005, 221.
[25] Bontemps, S.; Bouhadir, G.; Dyer, P. W.; Miqueu, K.; Bourissou, D. Inorg. Chem. 2007, 46, 5149.
[26] (a) Bontemps, S.; Bouhadir, G.; Gu, W.; Mercy, M.; Chen, C. H.; Foxman, B. M.; Maron, L.; Ozerov, O. V.; Bourissou, D. Angew. Chem., Int. Ed. 2008, 47, 1481.
(b) Sircoglou, M.; Bontemps, S.; Bouhadir, G.; Saffon, N.; Miqueu, K.; Gu, W. X.; Mercy, M.; Chen, C. H.; Foxman, B. M.; Maron, L.; Ozerov, O. V.; Bourissou, D. J. Am. Chem. Soc. 2008, 130, 16729.
(c) Kameo, H.; Hashimoto, Y.; Nakazawa, H. Organometallics 2012, 31, 4251.
(d) Suess, D. L. M.; Tsay, C.; Peters, J. C. J. Am. Chem. Soc. 2012, 134, 14158.
[27] Moret, M. E.; Peters, J. C. Angew. Chem., Int. Ed. 2011, 50, 2063.
[28] Sircoglou, M.; Bontemps, S.; Mercy, M.; Saffon, N.; Takahashi, M.; Bouhadir, G.; Maron, L.; Bourissou, D. Angew. Chem., Int. Ed. 2007, 46, 8583.
[29] Boone, M. P.; Stephan, D. W. J. Am. Chem. Soc. 2013, 135, 8508.
[30] (a) Schindler, T.; Lux, M.; Peters, M.; Scharf, L. T.; Osseili, H.; Maron, L.; Tauchert, M. E. Organometallics 2015, 34, 1978.
(b) Nesbit, M. A.; Suess, D. L. M.; Peters, J. C. Organometallics 2015, 34, 4741.
(c) Suess, D. L. M.; Peters, J. C. J. Am. Chem. Soc. 2013, 135, 12580.
(d) Sircoglou, M.; Bontemps, S.; Mercy, M.; Miqueu, K.; Ladeira, S.; Saffon, N.; Maron, L.; Bouhadir, G.; Bourissou, D. Inorg. Chem. 2010, 49, 3983.
(e) Kameo, H.; Nakazawa, H. Organometallics 2012, 31, 7476.
(f) Conifer, C. M.; Law, D. J.; Sunley, G. J.; White, A. J. P.; Britovsek, G. J. P. Organometallics 2011, 30, 4060.
[31] Bontemps, S.; Bouhadir, G.; Miqueu, K.; Bourissou, D. J. Am. Chem. Soc. 2006, 128, 12056.
[32] Cowie, B. E.; Emslie, D. J. H. Chem.-Eur. J. 2014, 20, 16899.
[33] Barnett, B. R.; Moore, C. E.; Rheingold, A. L.; Figueroa, J. S. J. Am. Chem. Soc. 2014, 136, 10262.
[34] (a) Braunschweig, H.; Radacki, K.; Seeler, F.; Whittell, G. R. Organometallics 2004, 23, 4178.
(b) Braunschweig, H.; Radacki, K.; Seeler, F.; Whittell, G. R., Organometallics 2006, 25, 4605.
[35] Bissinger, P.; Braunschweig, H.; Damme, A.; Dewhurst, R. D.; Kraft, K.; Kramer, T.; Radacki, K. Chem.-Eur. J. 2013, 19, 13402.
[36] Vondung, L.; Frank, N.; Fritz, M.; Alig, L.; Langer, R. Angew. Chem., Int. Ed. 2016, 55, 14448.
[37] Frank, N.; Hanau, K.; Flosdorf, K.; Langer, R., Dalton Trans. 2013, 42, 11252.
[38] MacMillan, S. N.; Harman, W. H.; Peters, J. C. Chem. Sci. 2014, 5, 590.
[39] Boone, M. P.; Stephan, D. W. Chem.-Eur. J. 2014, 20, 3333.
[40] Suess, D. L. M.; Peters, J. C. J. Am. Chem. Soc. 2013, 135, 4938.
[41] Inagaki, F.; Matsumoto, C.; Okada, Y.; Maruyama, N.; Mukai, C., Angew. Chem., Int. Ed. 2015, 54, 818.
[42] (a) Anderson, J. S.; Rittle, J.; Peters, J. C. Nature 2013, 501, 84.
(b) Anderson, J. S.; Moret, M. E.; Peters, J. C. J. Am. Chem. Soc. 2013, 135, 534.
(c) Moret, M. E.; Peters, J. C. J. Am. Chem. Soc. 2011, 133, 18118.
[43] (a) Baker, R. T.; Ovenall, D. W.; Calabrese, J. C.; Westcott, S. A.; Taylor, N. J.; Williams, I. D.; Marder, T. B. J. Am. Chem. Soc. 1990, 112, 9399.
(b) Knorr, J. R.; Merola, J. S. Organometallics 1990, 9, 3008.
[44] Hartwig, J. F.; Huber, S. J. Am. Chem. Soc. 1993, 115, 4908.
[45] Aldridge, S.; Al-Fawaz, A.; Calder, R. J.; Dickinson, A. A.; Willock, D. J.; Light, M. E.; Hursthouse, M. B. Chem. Commun. 2001, 1846.
[46] Wadepohl, H.; Arnold, U.; Pritzkow, H. Angew. Chem., Int. Ed. 1997, 36, 974.
[47] Rickard, C. E. F.; Roper, W. R.; Williamson, A.; Wright, L. J. Organometallics 2002, 21, 4862.
[48] (a) Aldridge, S.; Jones, C.; Gans-Eichler, T.; Stasch, A.; Kays, D. L.; Coombs, N. D.; Willock, D. J. Angew. Chem., Int. Ed. 2006, 45, 6118.
(b) De, S.; Pierce, G. A.; Vidovic, D.; Kays, D. L.; Coombs, N. D.; Jemmis, E. D.; Aldridge, S. Organometallics 2009, 28, 2961.
(c) Pierce, G. A.; Vidovic, D.; Kays, D. L.; Coombs, N. D.; Thompson, A. L.; Jemmis, E. D.; De, S.; Aldridge, S. Organometallics 2009, 28, 2947.
[49] Braunschweig, H.; Radacki, K.; Uttinger, K. Chem.-Eur. J. 2008, 14, 7858.
[50] (a) Curtis, D.; Lesley, M. J. G.; Norman, N. C.; Orpen, A. G.; Starbuck, J. J. Chem. Soc., Dalton Trans. 1999, 1687.
(b) Addy, D. A.; Phillips, N.; Pierce, G. A.; Vidovic, D.; Kramer, T.; Mallick, D.; Jemmis, E. D.; Reid, G.; Aldridge, S. Organometallics 2012, 31, 1092.
[51] (a) Segawa, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2007, 46, 6710.
(b) Asay, M.; Jones, C.; Driess, M. Chem. Rev. 2011, 111, 354.
(c) Frank, R.; Howell, J.; Campos, J.; Tirfoin, R.; Phillips, N.; Zahn, S.; Mingos, D. M. P.; Aldridge, S. Angew. Chem., Int. Ed. 2015, 54, 9586.
(d) Lu, W.; Hu, H. T.; Li, Y. X.; Ganguly, R.; Kinjo, R. J. Am. Chem. Soc. 2016, 138, 6650.
[52] Onozawa, S.-y.; Hatanaka, Y.; Sakakura, T.; Shimada, S.; Tanaka, M. Organometallics 1996, 15, 5450.
[53] (a) Borner, C.; Brandhorst, K.; Kleeberg, C. Dalton Trans. 2015, 44, 8600.
(b) Clark, G. R.; Irvine, G. J.; Roper, W. R.; Wright, L. J. J. Organomet. Chem. 2003, 680, 81.
(c) Habereder, T.; Noth, H. Appl. Organomet. Chem. 2003, 17, 525.
(d) Onozawa, S.; Tanaka, M. Organometallics 2001, 20, 2956.
(e) Okuno, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2011, 50, 920;
(f) Kajiwara, T.; Terabayashi, T.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2008, 47, 6606.
(g) Terabayashi, T.; Kajiwara, T.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2009, 131, 14162.
[54] (a) Kawamura, K.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 8422.
(b) Aldridge, S.; Calder, R. J.; Baghurst, R. E.; Light, M. E.; Hursthouse, M. B. J. Organomet. Chem. 2002, 649, 9.
(c) Braunschweig, H.; Bertermann, R.; Brenner, P.; Burzler, M.; Dewhurst, R. D.; Radacki, K.; Seeler, F. Chem.-Eur. J. 2011, 17, 11828.
(d) Esteruelas, M. A.; Lopez, A. M.; Mora, M.; Onate, E. Chem. Commun. 2013, 49, 7543.
[55] Braunschweig, H.; Chiu, C. W.; Radacki, K.; Brenner, P. Chem. Commun. 2010, 46, 916.
[56] Braunschweig, H.; Fernandez, I.; Frenking, G.; Radacki, K.; Seeler, F. Angew. Chem., Int. Ed. 2007, 46, 5215.
[57] (a) Segawa, Y.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2009, 131, 9201.
(b) Segawa, Y.; Yamashita, M.; Nozaki, K. Organometallics 2009, 28, 6234.
[58] Miyada, T.; Kwan, E. H.; Yamashita, M. Organometallics 2014, 33, 6760.
[59] Kwan, E. H.; Kawai, Y. J.; Kamakura, S.; Yamashita, M. Dalton Trans. 2016, 45, 15931.
[60] Hasegawa, M.; Segawa, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2012, 51, 6956.
[61] Ogawa, H.; Yamashita, M. Dalton Trans. 2013, 42, 625.
[62] Lin, T. P.; Peters, J. C. J. Am. Chem. Soc. 2014, 136, 13672.
[63] Tanoue, K.; Yamashita, M. Organometallics 2015, 34, 4011.
[64] Braunschweig, H.; Kollann, C.; Englert, U. Angew. Chem., Int. Ed. 1998, 37, 3179.
[65] Braunschweig, H.; Colling, M.; Kollann, C.; Stammler, H. G.; Neumann, B. Angew. Chem., Int. Ed. 2001, 40, 2298.
[66] Braunschweig, H.; Colling, M.; Hu, C. H.; Radacki, K. Angew. Chem., Int. Ed. 2003, 42, 205.
[67] Blank, B.; Colling-Hendelkens, M.; Kollann, C.; Radacki, K.; Rais, D.; Uttinger, K.; Whittell, G. R.; Braunschweig, H. Chem.-Eur. J. 2007, 13, 4770.
[68] Niemeyer, J.; Addy, D. A.; Riddlestone, I.; Kelly, M.; Thompson, A. L.; Vidovic, D.; Aldridge, S. Angew. Chem., Int. Ed. 2011, 50, 8908.
[69] O'Neill, M.; Addy, D. A.; Riddlestone, I.; Kelly, M.; Phillips, N.; Aldridge, S. J. Am. Chem. Soc. 2011, 133, 11500.
[70] Braunschweig, H.; Radacki, K.; Rais, D.; Schneider, A.; Seeler, F. J. Am. Chem. Soc. 2007, 129, 10350.
[71] Coombs, D. L.; Aldridge, S.; Jones, C.; Willock, D. J. J. Am. Chem. Soc. 2003, 125, 6356.
[72] Braunschweig, H.; Burzler, M.; Kupfer, T.; Radacki, K.; Seeler, F. Angew. Chem., Int. Ed. 2007, 46, 7785.
[73] Braunschweig, H.; Ye, Q.; Radacki, K. Chem. Commun. 2012, 48, 2701.
[74] Braunschweig, H.; Colling, M.; Kollann, C.; Merz, K.; Radacki, K. Angew. Chem., Int. Ed. 2001, 40, 4198.
[75] Braunschweig, H.; Kupfer, T.; Radacki, K.; Schneider, A.; Seeler, F.; Uttinger, K.; Wu, H. J. Am. Chem. Soc. 2008, 130, 7974.
[76] Braunschweig, H.; Radacki, K.; Rais, D.; Uttinger, K. Angew. Chem., Int. Ed. 2006, 45, 162.
[77] (a) Braunschweig, H.; Radacki, K.; Schneider, A. Science 2010, 328, 345.
(b) Braunschweig, H.; Radacki, K.; Schneider, A. Chem. Commun. 2010, 46, 6473.
[78] Alcaraz, G.; Helmstedt, U.; Clot, E.; Vendier, L.; Sabo-Etienne, S. J. Am. Chem. Soc. 2008, 130, 12878.
[79] Addy, D. A.; Bates, J. I.; Kelly, M. J.; Riddlestone, I. M.; Aldridge, S. Organometallics 2013, 32, 1583
(b) Franssen, N. M. G.; Walters, A. J. C.; Reek, J. N. H.; de Bruin, B. Catal. Sci. Technol. 2011, 1, 153.
(c) Souillart, L.; Cramer, N. Chem. Rev. 2015, 115, 9410.
(d) Gupta, K. C.; Sutar, A. K. Coord. Chem. Rev. 2008, 252, 1420.
(e) Wang, X. Y.; Zheng, X. M.; Hou, Z. Y. Chin. Chem. Lett. 1999,
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