Lewis Acid Transition-Metal-Catalyzed Hydrogen Activation: Structures, Mechanisms, and Reactivities.
Lewis acids
catalysis
hydrogen activation
mechanisms
synergetic catalysis
transition metals
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
28 Oct 2019
28 Oct 2019
Historique:
received:
12
07
2019
pubmed:
8
8
2019
medline:
8
8
2019
entrez:
8
8
2019
Statut:
ppublish
Résumé
As a new type of bifunctional catalyst, the Lewis acid transition-metal (LA-TM) catalysts have been widely applied for hydrogen activation. This study presents a mechanistic framework to understand the LA-TM-catalyzed H
Identifiants
pubmed: 31390099
doi: 10.1002/chem.201903193
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
13785-13798Subventions
Organisme : National Natural Science Foundation of China
ID : 21673301, 21973113, 21573292, and 21773312
Organisme : the Guangdong Natural Science Funds for Distinguished Young Scholars
ID : 2015A030306027
Organisme : the Tip-top Youth Talents of Guangdong special support program
ID : 20153100042090500
Organisme : the Fundamental Research Funds for the Central Universities
Organisme : National Natural Science Foundation of China
ID : 21673301, 21573292, and 21773312
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
D. M. Heinekey, A. Lledós, J. M. Lluch, Chem. Soc. Rev. 2004, 33, 175-182;
M. Torrent, M. Solà, G. Frenking, Chem. Rev. 2000, 100, 439-494;
S. Niu, M. B. Hall, Chem. Rev. 2000, 100, 353-406;
R. H. Crabtree, Chem. Rev. 2016, 116, 8750-8769.
S. Shima, O. Pilak, S. Vogt, M. Schick, M. S. Stagni, W. Meyer-Klaucke, E. Warkentin, R. K. Thauer, U. Ermler, Science 2008, 321, 572-575;
J. C. Fontecilla-Camps, A. Volbeda, C. Cavazza, Y. Nicolet, Chem. Rev. 2007, 107, 4273-4303.
Y. Shvo, D. Czarkie, J. Organomet. Chem. 1986, 315, C25-C28;
Y. Blum, D. Czarkie, Y. Rahamim, Y. Shvo, Organometallics 1985, 4, 1459-1461;
K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. Int. Ed. Engl. 1997, 36, 285-288;
R. Karvembu, R. Prabhakaran, K. Natarajan, Coord. Chem. Rev. 2005, 249, 911-918.
I. Kuzu, I. Krummenacher, J. Meyer, F. Armbruster, F. Breher, Dalton Trans. 2008, 5836-5865.
H. Song, B. Kang, S. H. Hong, ACS Catal. 2014, 4, 2889-2895;
G. Zhang, S. K. Hanson, Org. Lett. 2013, 15, 650-653;
D. S. Matharu, D. J. Morris, G. J. Clarkson, M. Wills, Chem. Commun. 2006, 3232-3234;
K. Abdur-Rashid, S. E. Clapham, A. Hadzovic, J. N. Harvey, A. J. Lough, R. H. Morris, J. Am. Chem. Soc. 2002, 124, 15104-15118;
E. B. Hulley, K. D. Welch, A. M. Appel, D. L. DuBois, R. M. Bullock, J. Am. Chem. Soc. 2013, 135, 11736-11739.
S. E. Clapham, A. Hadzovic, R. H. Morris, Coord. Chem. Rev. 2004, 248, 2201-2237;
J. S. M. Samec, J.-E. Bäckvall, P. G. Andersson, P. Brandt, Chem. Soc. Rev. 2006, 35, 237-248.
G. C. Welch, R. R. S. Juan, J. D. Masuda, D. W. Stephan, Science 2006, 314, 1124-1126;
D. W. Stephan, Org. Biomol. Chem. 2008, 6, 1535-1539;
D. W. Stephan, J. Am. Chem. Soc. 2015, 137, 10018-10032;
T. Wiegand, H. Eckert, O. Ekkert, R. Fröhlich, G. Kehr, G. Erker, S. Grimme, J. Am. Chem. Soc. 2012, 134, 4236-4249;
T. A. Rokob, I. Bakó, A. Stirling, A. Hamza, I. Pápai, J. Am. Chem. Soc. 2013, 135, 4425-4437;
G. Lu, H. Li, L. Zhao, F. Huang, Z.-X. Wang, Inorg. Chem. 2010, 49, 295-301;
Y. Shao, J. Zhang, Y. Li, Y. Liu, Z. Ke, Org. Lett. 2018, 20, 1102-1105.
A. Amgoune, D. Bourissou, Chem. Commun. 2011, 47, 859-871;
H. Braunschweig, R. D. Dewhurst, Dalton Trans. 2011, 40, 549-558;
J. R. Khusnutdinova, D. Milstein, Angew. Chem. Int. Ed. 2015, 54, 12236-12273;
Angew. Chem. 2015, 127, 12406-12445;
G. R. Owen, Chem. Commun. 2016, 52, 10712-10726;
G. Bouhadir, D. Bourissou, Chem. Soc. Rev. 2016, 45, 1065-1079;
R. C. Cammarota, L. J. Clouston, C. C. Lu, Coord. Chem. Rev. 2017, 334, 100-111.
Y. Li, J. Liu, C. Hou, Y. Shao, L.-B. Qu, C. Zhao, Z. Ke, Catal. Sci. Technol. 2018, 8, 3395-3405;
Y. Li, J. Zhang, S. Shu, Y. Shao, Y. Liu, Z. Ke, Chin. J. Org. Chem. 2017, 37, 2187-2202.
T.-P. Lin, J. C. Peters, J. Am. Chem. Soc. 2014, 136, 13672-13683;
M. Devillard, E. Nicolas, A. W. Ehlers, J. Backs, S. Mallet-Ladeira, G. Bouhadir, J. C. Slootweg, W. Uhl, D. Bourissou, Chem. Eur. J. 2015, 21, 74-79;
N. Curado, C. Maya, J. López-Serrano, A. Rodríguez, Chem. Commun. 2014, 50, 15718-15721;
S. K. Podiyanachari, R. Fröhlich, C. G. Daniliuc, J. L. Petersen, C. Mück-Lichtenfeld, G. Kehr, G. Erker, Angew. Chem. Int. Ed. 2012, 51, 8830-8833;
Angew. Chem. 2012, 124, 8960-8963;
H. Kameo, T. Kawamoto, D. Bourissou, S. Sakaki, H. Nakazawa, Organometallics 2015, 34, 1440-1448.
N. Tsoureas, Y.-Y. Kuo, M. F. Haddow, G. R. Owen, Chem. Commun. 2011, 47, 484-486.
W. H. Harman, J. C. Peters, J. Am. Chem. Soc. 2012, 134, 5080-5082;
W. H. Harman, T.-P. Lin, J. C. Peters, Angew. Chem. Int. Ed. 2014, 53, 1081-1086;
Angew. Chem. 2014, 126, 1099-1104.
M. Toure, O. Chuzel, J.-L. Parrain, Dalton Trans. 2015, 44, 7139-7143;
K. Tanoue, M. Yamashita, Organometallics 2015, 34, 4011-4017;
T. Schindler, M. Lux, M. Peters, L. T. Scharf, H. Osseili, L. Maron, M. E. Tauchert, Organometallics 2015, 34, 1978-1984;
F. Inagaki, C. Matsumoto, Y. Okada, N. Maruyama, C. Mukai, Angew. Chem. Int. Ed. 2015, 54, 818-822;
Angew. Chem. 2015, 127, 832-836;
R. C. Cammarota, C. C. Lu, J. Am. Chem. Soc. 2015, 137, 12486-12489;
B. E. Cowie, D. J. H. Emslie, Organometallics 2015, 34, 4093-4101;
M. P. Boone, D. W. Stephan, J. Am. Chem. Soc. 2013, 135, 8508-8511;
H. Kameo, H. Nakazawa, Organometallics 2012, 31, 7476-7484;
E. J. Derrah, M. Sircoglou, M. Mercy, S. Ladeira, G. Bouhadir, K. Miqueu, L. Maron, D. Bourissou, Organometallics 2011, 30, 657-660;
M. V. Vollmer, J. Xie, C. C. Lu, J. Am. Chem. Soc. 2017, 139, 6570-6573.
H. Fong, M.-E. Moret, Y. Lee, J. C. Peters, Organometallics 2013, 32, 3053-3062.
T.-P. Lin, J. C. Peters, J. Am. Chem. Soc. 2013, 135, 15310-15313.
B. R. Barnett, C. E. Moore, A. L. Rheingold, J. S. Figueroa, J. Am. Chem. Soc. 2014, 136, 10262-10265.
G. Zeng, S. Sakaki, Inorg. Chem. 2013, 52, 2844-2853;
Y. Li, C. Hou, J. Jiang, Z. Zhang, C. Zhao, A. J. Page, Z. Ke, ACS Catal. 2016, 6, 1655-1662;
I. M. Riddlestone, N. A. Rajabi, J. P. Lowe, M. F. Mahon, S. A. Macgregor, M. K. Whittlesey, J. Am. Chem. Soc. 2016, 138, 11081-11084.
A. D. Becke, J. Chem. Phys. 1993, 98, 1372-1377.
C. Hou, J. Jiang, Y. Li, Z. Zhang, C. Zhao, Z. Ke, Dalton Trans. 2015, 44, 16573-16585.
G. Ganguly, T. Malakar, A. Paul, ACS Catal. 2015, 5, 2754-2769.
R. Shannon, Acta Crystallogr. Sect. A 1976, 32, 751-767.
H. Schubert, W. Leis, H. A. Mayer, L. Wesemann, Chem. Commun. 2014, 50, 2738-2740;
T. Habereder, H. Nöth, Appl. Organomet. Chem. 2003, 17, 525-538.
M. Devillard, R. Declercq, E. Nicolas, A. W. Ehlers, J. Backs, N. Saffon-Merceron, G. Bouhadir, J. C. Slootweg, W. Uhl, D. Bourissou, J. Am. Chem. Soc. 2016, 138, 4917-4926.
P. Hohenberg, W. Kohn, Phys. Rev. 1964, 136, B864-B871.
Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215-241.
F. Weigend, Phys. Chem. Chem. Phys. 2006, 8, 1057-1065;
F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
H. Lin, D. G. Truhlar, Theor. Chem. Acc. 2007, 117, 185;
H. M. Senn, W. Thiel, Angew. Chem. Int. Ed. 2009, 48, 1198-1229;
Angew. Chem. 2009, 121, 1220-1254;
L. C. Menikarachchi, J. A. Gascon, Curr. Top. Med. Chem. 2010, 10, 46-54.
S. Dapprich, I. Komáromi, K. S. Byun, K. Morokuma, M. J. Frisch, J. Mol. Struct. 1999, 461-462, 1-21;
T. Vreven, K. S. Byun, I. Komáromi, S. Dapprich, J. A. Montgomery, K. Morokuma, M. J. Frisch, J. Chem. Theory Comput. 2006, 2, 815-826;
L. W. Chung, W. M. C. Sameera, R. Ramozzi, A. J. Page, M. Hatanaka, G. P. Petrova, T. V. Harris, X. Li, Z. Ke, F. Liu, H.-B. Li, L. Ding, K. Morokuma, Chem. Rev. 2015, 115, 5678-5796.
A. K. Rappe, C. J. Casewit, K. S. Colwell, W. A. Goddard, W. M. Skiff, J. Am. Chem. Soc. 1992, 114, 10024-10035.
A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113, 4538-4543.
NBO Version 3.1, E. D. Glendening, A. E. Reed, J. E. Carpenter, F. Weinhold.
Gaussian 09, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Inc. Gaussian, Wallingford CT, 2013.
C. Y. Legault, CYLview, 1.0b; Université de Sherbrooke 2009, http://www.cylview.org.