Hydroalkoxylation Catalyzed by a Gold(I) Complex Encapsulated in a Supramolecular Host

被引:183
作者
Wang, Z. Jane
Brown, Casey J.
Bergman, Robert G. [1 ]
Raymond, Kenneth N.
Toste, F. Dean
机构
[1] Univ Calif Berkeley, Lawrence Berkeley Lab, Div Chem Sci, Berkeley, CA 94720 USA
关键词
AZA-COPE REARRANGEMENT; H BOND ACTIVATION; INTERMOLECULAR HYDROALKOXYLATION; ALLENES; GUEST; REACTIVITY; MECHANISM; SCOPE;
D O I
10.1021/ja202055v
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Gold(I)-phosphine complexes are readily encapsulated by a tetrahedral supramolecular host (Ga4L6). We have investigated the catalytic activity of the resulting complexes for the intramolecular hydroalkoxylation of allenes. The catalytic activity of Me3PAuBr was increased 8-fold by encapsulation, as determined by initial rate kinetics, and we observed up to 67 catalytic turnovers by Me3PAu+ encapsulated in Ga4L6.
引用
收藏
页码:7358 / 7360
页数:3
相关论文
共 35 条
[11]   Regioselective Synthesis of tert-Allylic Ethers via Gold(I)-Catalyzed Intermolecular Hydroalkoxylation of Allenes [J].
Hadfield, Maximillian S. ;
Lee, Ai-Lan .
ORGANIC LETTERS, 2010, 12 (03) :484-487
[12]  
Hamilton GL, 2007, SCIENCE, V317, P496, DOI 10.1126/science.1145229
[13]   Homogeneous Gold Catalysis Beyond Assumptions and Proposals-Characterized Intermediates [J].
Hashmi, A. Stephen K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) :5232-5241
[14]   Aza cope rearrangement of propargyl enammonium cations catalyzed by a self-assembled "nanozyme" [J].
Hastings, Courtney J. ;
Fiedler, Dorothea ;
Bergman, Robert G. ;
Raymond, Kenneth N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (33) :10977-10983
[15]   Enzymelike Catalysis of the Nazarov Cyclization by Supramolecular Encapsulation [J].
Hastings, Courtney J. ;
Pluth, Michael D. ;
Bergman, Robert G. ;
Raymond, Kenneth N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) :6938-+
[16]   Acceleration of a Diels-Alder reaction by a self-assembled molecular capsule [J].
Kang, JM ;
Rebek, J .
NATURE, 1997, 385 (6611) :50-52
[17]   Gold-Catalyzed Nucleophilic Cyclization of Functionalized Allenes: A Powerful Access to Carbo- and Heterocycles [J].
Krause, Norbert ;
Winter, Christian .
CHEMICAL REVIEWS, 2011, 111 (03) :1994-2009
[18]   High-precision catalysts: Regioselective hydroformylation of internal alkenes by encapsulated rhodium complexes [J].
Kuil, Mark ;
Soltner, Theresa ;
van Leeuwen, Piet W. N. M. ;
Reek, Joost N. H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (35) :11344-11345
[19]   Gold(I)-Catalyzed Enantioselective Synthesis of Pyrazolidines, Isoxazolidines, and Tetrahydrooxazines [J].
LaLonde, R. L. ;
Wang, Z. J. ;
Mba, M. ;
Lackner, A. D. ;
Toste, F. Dean .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (03) :598-601
[20]   Highly selective supramolecular catalyzed allylic alcohol isomerization [J].
Leung, Dennis H. ;
Bergman, Robert G. ;
Raymond, Kenneth N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (10) :2746-+