Advances in Hydrogenation of Carboxylic Acid Derivatives and CO2 Using Triphos as the Coordination Ligand
- Corresponding author: Ding Kuiling, kding@sioc.ac.cn
Citation:
Zhang Linli, Han Zhaobin, Zhang Lei, Li Mingxing, Ding Kuiling. Advances in Hydrogenation of Carboxylic Acid Derivatives and CO2 Using Triphos as the Coordination Ligand[J]. Chinese Journal of Organic Chemistry,
;2016, 36(8): 1824-1838.
doi:
10.6023/cjoc201603014
Gribble, G. W. Chem. Soc. Rev. 1998, 27, 395.(b) Seyden-Penne, J. Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2nd ed.; Wiley, New York, 1997.
Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.(b) Blaser, H.-U.; Federsel, H.-J. Asymmetric Catalysis on Industrial Scale, 2nd ed., Weinheim, Wiley-VCH, 2010.
McAlees, A. J.; McCrindle, R. J. Chem. Soc. C 1969, 2425.
Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kühn, F. E. Angew. Chem., Int. Ed. 2011, 50, 8510.(b) Zhang, L.; Han, Z.; Zhao, X.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2015, 54, 6186.
Wang, W. H.; Himeda, H.; Muckerman, J. T.; Manbeck, G. F.; Fujita, F. Chem. Rev. 2015, 115, 12936.
Nishimura, S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley, New York, 2001.
Rieke, R.; Thakur, D.; Roberts, B.; White, G. J. Am. Oil Chem. 1997, 74, 333.
de Vries, J. G.; Elsevier, C. J. The Handbook of Homogeneous Hydrogenation, Wiley, Weinheim, 2007.
Grey, R. A.; Pez, G. P.; Wallo, A. J. Am. Chem. Soc. 1981, 103, 7536.
Matteoli, U.; Menchi, G.; Bianchi, M.; Piacenti, F. J. Mol. Catal. 1988, 44, 347.
Teunissen, H. T.; Elsevier, C. J. Chem. Commun. 1997, 667.
Hewertson, W.; Watson, H. R. J. Chem. Soc. 1962, 1490.
van Engelen, M. C.; Teunissen, H. T.; de Vries, J. G.; Elsevier, C. J. J. Mol. Catal. A: Chem. 2003, 206, 185.
Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Zanobini, F. Coord. Chem. Rev. 1992, 120, 193.(b) Hierso, J.-C.; Amardeil, R.; Bentabet, E.; Broussier, R.; Gautheron, B.; Meunier, P.; Kalck, P. Coord. Chem. Rev. 2003, 236, 143.
Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Frediani, P.; Ramirez, J. A. Organometallics 1990, 9, 226.
Barbaro, P.; Bianchini, C.; Meli, A.; Moreno, M.; Vizza, F. Organometallics 2002, 21, 1430.
Bianchini, C.; Meli, A.; Moneti, S.; Vizza, F. Organometallics 1998, 17, 2636.(b) Bianchini, C.; Masi, D.; Meli, A.; Peruzzini, M.; Vizza, F.; Zanobini, F. Organometallics 1998, 17, 2495.(c) Bianchini, C.; Meli, A.; Vizza, F. J. Organomet. Chem. 2004, 689, 4277.
Barbaro, P.; Bianchini, C.; Frediani, P.; Meli, A.; Vizza, F. Inorg. Chem. 1992, 31, 1523.
Mellone, I.; Bertini, F.; Gonsalvi, L.; Guerriero, A.; Peruzzini, M. Chimia 2015, 69, 331.
Dub, P. A.; Ikariya, T. ACS Catal. 2012, 2, 1718.(b) Werkmeister, S.; Neumann, J.; Junge, K.; Beller, M. Chem. Eur. J. 2015, 21, 12226.
Teunissen, H. T.; Elsevier, C. J. Chem. Commun. 1998, 1367.
Berke, H. Book of Abstracts, XⅡth FECHEM Conference on Organometallic Chemistry, Prague, 1997, PL 9.
Rosato, D. V.; Rosato, M. V. Plastic Product Material and Process Selection Handbook, Elsevier, North Holland, 2004.
Furst, M. R. L.; Goff, R. L.; Quinzler, D.; Mecking, S.; Botting C. H.; Cole-Hamilon D. J. Green Chem. 2012, 12, 472.
vom Stein, T.; Meuresch, M.; Limper, D.; Schmitz, M.; Hölscher; Coetzee, J.; Cole-Hamilton, D. J.; Klankermayer, J.; Leitner, W. J. Am. Chem. Soc. 2014, 136, 13217.
Wesselbaum, S.; vom Stein, T.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2012, 51, 7499.
Boardman, B.; Hanton, M. J.; van Rensburg, H.; Tooze, R. P. Chem. Commun. 2006, 2289.
Hanton, M. J.; Tin, S.; Boardman, B. J.; Miller, P. J. Mol. Catal. A: Chem. 2011, 346, 70.
Li, Y. H.; Topf, C.; Cui, X. J.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2015, 54, 5196.
Kilner, M.; Tyers, D. V.; Crabtree, S. P.; Wood, M. A. US 7709689, 2003 [Chem. Abstr. 2003, 139, 366612].
Crabtree, S. P.; Tyers, D. V.; Sharif, M. WO 05/051907, 2005 [Chem. Abstr. 2005, 143, 43765].
Rosi, L.; Frediani, M.; Frediani, P. J. Organomet. Chem. 2010, 695, 1314.
Geilen, F. M. A.; Engendahl, B.; Harwardt, A.; Marquardt, W.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2010, 49, 5510.
Geilen, F. M. A.; Engendahl, B.; Hölscher, M.; Klankermayer, J.; Leitner, W. J. Am. Chem. Soc. 2011, 133, 14349.
Phanopoulos, A.; White, A. J. P.; Long, N. J.; Miller, P. W. ACS Catal. 2015, 5, 2500.
Cui, X. J.; Li, Y. H.; Topf, C.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2015, 54, 10596.
Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411.
Magro, A. A. N.; Eastham, G. R.; Cole-Hamilton, D. J. Chem. Commun. 2007, 3154.
Dodds, D. L.; Coetzee, J.; Klankermayer, J.; Brosinski, S.; Leitner, W.; Cole-Hamilton, D. J. Chem. Commun. 2012, 48, 12249.
Coetzee, J.; Dodds, D. L.; Klankermayer, J.; Brosinski, S.; Leitner, W.; Slawin, A. M. Z.; Col-Hamilton, D. J. Chem. Eur. J. 2013, 19, 11039.
Cabrero-Antonino, J. R.; Alberico, E.; Junge, K.; Junge, H.; Beller M. Chem. Sci. 2016, 7, 3432.
Meuresch, M.; Westhues, S.; Leitner, W.; Klankermayer, J. Angew. Chem., Int. Ed. 2016, 55, 1392.
Cabrero-Antonino, J. R.; Sorribes, I.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2016, 55, 387.
Huff, C. A.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18122.(b) Li, Y. N.; He, L. N.; Liu, A. H.; Lang, X. D.; Yang, Z. Z.; Yu, B.; Luan, C. R. Green Chem. 2013, 15, 2825.(c) Khusnutdinova, J. R.; Garg, J. A.; Milstein, D. ACS Catal. 2015, 5, 2416.(d) Kothandaraman, J.; Goeppert, A.; Czaun, M.; Olah, G. A.; Prakash, G. K. S. J. Am. Chem. Soc. 2016, 138, 778.
Wesselbaum, S.; Moha, V.; Meuresch, M.; Brosinski, S.; Thenert, K. M.; Kothe, J.; vom Stein, T.; Englert, U.; Holscher, M.; Klankermayer, J.; Leitner, W. Chem. Sci. 2015, 6, 693.
Beydoun, K.; vom Stein, T.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2013, 52, 9554.
Li, Y.; Sorribes, I.; Yan, T.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 12156.
Beydoun, K.; Ghattas, G.; Thenert, K.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2014, 53, 11010.
Beydoun, K.; Thenert, K.; Streng, E. S.; Brosinski, S.; Leitner, W.; Klankermayer, J. ChemCatChem 2016, 8, 135
Li, Y.; Yan, T.; Junge, K.; Beller M. Angew. Chem., Int. Ed. 2014, 53, 10476.
Savourey, S.; Lefevre, G.; Berthet, J.-C.; Cantat, T. Chem. Commun. 2014, 50, 14033.
Sorribes, I.; Cabrero-Antonino, J. R.; Vicent, C.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2015, 137, 13580.
Korstanje, T. J.; van der Vlugt, J. I.; Elsevier, C. J.; de Bruin, B. Science 2015, 350, 298.
Zall, C. M.; Linehan, J. C.; Appel A. M. ACS Catal. 2015, 5, 5301.
Watari, R.; Kayaki, Y.; Hirano, S.; Matsumoto, N.; Ikariya, T. Adv. Synth. Catal. 2015, 357, 1369.
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