Chinese Journal of Organic Chemistry >
Progress of Frustrated Lewis Pairs in Catalytic Hydrogenation
Received date: 2016-07-30
Revised date: 2016-09-19
Online published: 2016-11-03
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21276238, 21676253).
Frustrated Lewis pairs (FLPs) catalyzed hydrogenation reaction is one of the hotspots in the current hydrogenation field. This kind of reaction has the advantages of environment friendly, no metal residue, etc., and has a potential prospect for industrial application. According to the category of the substrate, a brief review of the recent progress in the field of the FLPs-catalyzed hydrogenation as well as the asymmetric hydrogenation is depicted.
Wang Hui , Zheng Yi , Pan Zhentao , Fu Hongliang , Ling Fei , Zhong Weihui . Progress of Frustrated Lewis Pairs in Catalytic Hydrogenation[J]. Chinese Journal of Organic Chemistry, 2017 , 37(2) : 301 -313 . DOI: 10.6023/cjoc201607046
[1] Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124.
[2] Spies, P.; Erker, G.; Kehr, G.; Bergander, K.; Fröhlich, R.; Grimme, S.; Stephan, D.W. Chem. Commun. 2007, 5072.
[3] Sumerin, V.; Schulz, F.; Nieger, M.; Leskelä, M.; Repo, T.; Rieger, B. Angew. Chem. Int. Ed. 2008, 47, 6001.
[4] Holschumacher, D.; Bannenberg, T.; Hrib, C. G.; Jones, P. G.; Tamm, M. Angew. Chem. Int. Ed. 2008, 47, 7428.
[5] Lu, Z.-P.; Cheng, Z.-H.; Chen, Z.-X.; Weng, L.-H.; Li, Z.-H.; Wang, H.-D. Angew. Chem., Int. Ed. 2011, 50, 12227.
[6] Zaher, H.; Ashley, A. E.; Irwin, M.; Thompson, A. L.; Gutmann, M. J.; Krämer, T.; O'Hare, D. Chem. Commun., 2013, 49, 9755.
[7] Caputo, C. B.; Zhu, K.-L.; Vukotic, V. N.; Loeb, S. J.; Stephan, D. W. Angew. Chem. Int. Ed. 2013, 52, 960.
[8] Chernichenko, K.; Kótai, B.; Pápai, I.; Zhivonitko, V.; Nieger, M.; Leskelä, M.; Repo; T. Angew. Chem., Int. Ed. 2015, 54, 1749.
[9] Samigullin, K.; Georg, I.; Bolte, M.; Lerner, H. W.; Wagner, M. Chem. Eur. J. 2016, 22, 3478.
[10] Zheng, J.-H.; Lin, Y.-J.; Wang, H.-D. Dalton Trans. 2016, 45, 6088.
[11] Mo, Z.-B.; Rit, A.; Campos, J.; Kolychev, E. L.; Aldridge, S. J. Am. Chem. Soc. 2016, 138, 3306.
[12] Wang, P.-A.; Sun, X.-L.; Gao, P. Chin. J. Org. Chem. 2011, 31, 1369 (in Chinese).(王平安, 孙晓莉, 高鹏, 有机化学, 2011, 31, 1369.)
[13] Xu, Y.-Y.; Li, Z.; Maxim B.; Nie, W.-L. Prog. Chem. 2012, 24, 1526 (in Chinese).(徐莹莹, 李钊, Maxim B., 聂万丽, 化学进展, 2012, 24, 1526.)
[14] Chase, P. A.; Welch, G. C.; Jurca, T.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 8050.
[15] Chase, P. A.; Jurca, T.; Stephan, D. W. Chem. Commun. 2008, 1701.
[16] Mohr, J.; Oestreich, M. Angew. Chem., Int. Ed. 2014, 53, 13278.
[17] Wei, S.-M.; Feng, X.-Q.; Du, H.-F. Org. Biomol. Chem. 2016, 14, 8026.
[18] Farrell, J. M.; Heiden, Z. M.; Stephan, D. W. Organometallics 2011, 30, 4497.
[19] Chatterjee, I.; Oestreich, M. Angew. Chem., Int. Ed. 2015, 54, 1965.
[20] Jiang, C.-F.; Blacque, O.; Berke, H. Chem. Commun. 2009, 5518.
[21] Scott, D. J.; Fuchter, M. J.; Ashley, A. E. Angew. Chem., Int. Ed. 2014, 53, 10218.
[22] Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Fröhlich, R.; Erker, G. Angew. Chem., Int. Ed. 2008, 47, 7543.
[23] Wang, G.; Chen, C.; Du, T.-Y.; Zhong, W.-H. Adv. Synth. Catal. 2014, 356, 1747.
[24] (a) Sumerin, V.; Chernichenko, K.; Nieger, M.; Leskelä, M.; Rieger, B.; Repo, T. Adv. Synth. Catal. 2011, 353, 2093.
(b) Chernichenko, K.; Nieger, M.; Leskelä, M.; Repo, T. Dalton Trans. 2012, 41, 9029.
(c) Sumerin, V.; Schulz, F.; Atsumi, M.; Wang, C.; Nieger, M.; Leskelä, M.; Repo, T.; Pyykkö, P.; Rieger, B. J. Am. Chem. Soc. 2008, 130, 14117.
[25] Farrell, J. M.; Posaratnanathan, R. T.; Stephan, D. W. Chem. Sci. 2015, 6, 2010.
[26] Mummadi, S.; Unruh, D. K.; Zhao, J.-Y.; Li, S.-H.; Krempner, C. J. Am. Chem. Soc. 2016, 138, 3286.
[27] Schwendemann, S.; Frölich, R.; Kehr, G.; Erker, G. Chem. Sci. 2011, 2, 1842.
[28] (a) Parks, D. J.; Spence, R. E. v. H.; Piers, W. E. Angew. Chem., Int. Ed. Engl. 1995, 34, 809.
(b) Parks, D. J.; Piers, W. E.; Yap, G. P. A. Organometallics 1998, 17, 5492.
[29] Wang, H.-D.; Fröhlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2008, 5966.
[30] Greb, L.; Oña-Burgos, P.; Schirmer, B.; Grimme, S.; Stephan, D. W.; Paradies, J. Angew. Chem., Int. Ed. 2012, 51, 10164.
[31] Erõs, G.; Mehdi, H.; Pápai, I.; Rokob, T. A.; Király, P.; Tárkányi, G.; Soós, T. Angew. Chem., Int. Ed. 2010, 49, 6559.
[32] Inés, B.; Palomas, D.; Holle, S.; Steinberg, S.; Nicasio, J. A.; Alcarazo, M. Angew. Chem., Int. Ed. 2012, 51, 12367.
[33] (a) Greb, L.; Daniliuc, C. G.; Bergander, K.; Paradies, J. Angew. Chem., Int. Ed. 2013, 52, 5876.
(b) Paradies, J. Angew. Chem., Int. Ed. 2014, 53, 3552.
[34] Hounjet, L. J.; Bannwarth, C.; Garon, C. N.; Caputo, C. B.; Grimme, S.; Stephan, D. W. Angew. Chem., Int. Ed. 2013, 52, 7492.
[35] Wang, X.-W.; Kehr, G.; Daniliuc, C. G.; Erker, G. J. Am. Chem. Soc. 2014, 136, 3293.
[36] Chernichenko, K.; Madarász, Á.; Pápai, I.; Nieger, M.; Leskelä, M.; Repo, T. Nat. Chem. 2013, 5, 718.
[37] Szeto, K. C.; Sahyoun, W.; Merle, N.; Castelbou, J. L.; Popoff, N.; Lefebvre, F.; Raynaud, J.; Godard, C.; Claver, C.; Delevoye, L.; Gauvinc, R. M.; Taoufik, M. Catal. Sci. Technol. 2016, 6, 882.
[38] Reddy, J. S.; Xu, B.-H.; Mahdi, T.; Fröhlich, R.; Kehr, G.; Stephan, D. W.; Erker, G. Organometallics 2012, 31, 5638.
[39] Greb, L.; Oña-Burgos, P.; Kubas, A.; Falk, F. C.; Breher, F.; Finkc, K.; Paradies, J. Dalton Trans. 2012, 41, 9056.
[40] Longobardi, L. E.; Tang, C.; Stephan, D. W. Dalton Trans. 2014, 43, 15723.
[41] Mahdi, T.; Stephan, D. W. J. Am. Chem. Soc. 2014, 136, 15809.
[42] Scott, D. J.; Fuchter, M. J.; Ashley, A. E. J. Am. Chem. Soc. 2014, 136, 15813.
[43] Mahdi, T.; Stephan, D. W. Angew. Chem., Int. Ed. 2015, 54, 8511.
[44] Gyömöre, Á.; Bakos, M.; Földes, T.; Pápai, I.; Domján, A.; Soós, T. ACS Catal. 2015, 5, 5366.
[45] Geier, S. J.; Chase, P. A.; Stephan, D. W. Chem. Commun. 2010, 46, 4884.
[46] Erös, G.; Nagy, K.; Mehdi, H.; Pápai, I.; Nagy, P.; Király, P.; Tárkányi, G.; Soós, T. Chem. Eur. J. 2012, 18, 574.
[47] Chen, B.-L.; Wang, B.; Lin, G.-Q. J. Org. Chem. 2010, 75, 941.
[48] Segawa, Y.; Stephan, D. W. Chem. Commun. 2012, 48, 11963.
[49] Mahdi, T.; Heiden, Z. M.; Grimme, S.; Stephan, D. W. J. Am. Chem. Soc. 2012, 134, 4088.
[50] Longobardi, L. E.; Mahdi, T.; Stephan, D. W. Dalton Trans. 2015, 44, 7114.
[51] Mahdi, T.; Castillo, J. N. D.; Stephan, D. W. Organometallics 2013, 32, 1971.
[52] Liu, Y.-B.; Du, H.-F. J. Am. Chem. Soc. 2013, 135, 12968.
[53] Liu Y. -B., Du H. -F. Acta Chim. Sinica 2014, 72, 771 (in Chinese).(刘勇兵, 杜海峰, 化学学报, 2014, 72, 771.)
[54] Chen, D.-J.; Klankermayer, J. Chem. Commun. 2008, 2130.
[55] Chen, D.-J.; Wang, Y.-T.; Klankermayer, J. Angew. Chem., Int. Ed. 2010, 49, 9475.
[56] Ghattas, G.; Chen, D.-J.; Pan, F.-F.; Klankermayer, J. Dalton Trans. 2012, 41, 9026.
[57] Chen, D.-J.; Leich, V.; Pan, F.-F.; Klankermayer, J. Chem. Eur. J. 2012, 18, 5184.
[58] Lindqvist, M.; Borre, K.; Axenov, K.; Kótai, B.; Nieger, M.; Leskelä, M.; Pápai, I.; Repo, T. J. Am. Chem. Soc. 2015, 137, 4038.
[59] (a) Mewald, M.; Oestreich, M. Chem. Eur. J. 2012, 18, 14079.
(b) Hermeke, J.; Mewald, M.; Oestreich, M. J. Am. Chem. Soc. 2013, 135, 17537.
[60] Süsse, L.; Hermeke, J.; Oestreich, M. J. Am. Chem. Soc. 2016, 138, 6940.
[61] Liu, Y.-B.; Du, H.-F. J. Am. Chem. Soc. 2013, 135, 6810.
[62] Wei, S.-M.; Du, H.-F. J. Am. Chem. Soc. 2014, 136, 12261.
[63] Ren, X.-Y.; Li, G.; Wei, S.-M.; Du, H.-F. Org. Lett. 2015, 17, 990.
[64] Ren, X.-Y.; Du, H.-F. J. Am. Chem. Soc. 2016, 138, 810.
[65] Ashley, A. E.; Thompson, A. L.; O'Hare, D. Angew. Chem., Int. Ed. 2009, 48, 9839.
[66] Caputo, C. B.; Hounjet, L. J.; Dobrovetsky, R.; Stephan, D. W. Science 2013, 341, 1374.
[67] Hounjet, L. J.; Caputo, C. B.; Stephan, D. W. Dalton Trans. 2013, 42, 2629.
[68] Porwal, D.; Oestreich, M. Eur. J. Org. Chem. 2016, 3307.
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