Gold-Gold Cooperation in the Addition of Methanol to Alkynes

被引:69
作者
Roithova, Jana [1 ]
Jankova, Stepanka [1 ]
Jasikova, Lucie [1 ]
Vana, Jiri [1 ]
Hybelbauerova, Simona [1 ]
机构
[1] Charles Univ Prague, Fac Sci, Dept Organ Chem, Prague 12843 2, Czech Republic
基金
欧洲研究理事会;
关键词
density functional calculations; gold catalysis; ion spectroscopy; kinetics; reaction intermediates; CATALYZED SYNTHESIS; DUAL-ACTIVATION; CYCLIZATIONS; COUNTERION; REACTIVITY; COMPLEXES;
D O I
10.1002/anie.201204003
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The gold(I)-mediated reaction between an internal alkyne and methanol proceeds by a dual activation mechanism, which directly results in formation of gem-diaurated intermediates. Reaction intermediates were investigated by IR multiphoton dissociation spectroscopy, kinetics by NMR spectroscopy, and the mechanism by DFT calculations. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8378 / 8382
页数:5
相关论文
共 57 条
[1]   Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters:: The mPW and mPW1PW models [J].
Adamo, C ;
Barone, V .
JOURNAL OF CHEMICAL PHYSICS, 1998, 108 (02) :664-675
[2]  
[Anonymous], 2003, ANGEW CHEM, DOI DOI 10.1002/ANGE.200200560
[3]  
[Anonymous], 2009, Angew. Chem
[4]  
[Anonymous], ANGEW CHEM
[5]  
[Anonymous], 2012, ANGEW CHEM
[6]   Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes [J].
Aubert, Corinne ;
Fensterbank, Louis ;
Garcia, Pierre ;
Malacria, Max ;
Simonneau, Antoine .
CHEMICAL REVIEWS, 2011, 111 (03) :1954-1993
[7]   Gold-mediated C-H bond functionalisation [J].
Boorman, Tanya C. ;
Larrosa, Igor .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1910-1925
[8]  
Burke K., 1998, ELECT DENSITY FUNCTI
[9]   Electrospray ionization tandem mass spectrometry in high-throughput screening of homogeneous catalysts [J].
Chen, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (25) :2832-2847
[10]   Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction [J].
Cheong, Paul Ha-Yeon ;
Morganelli, Philip ;
Luzung, Michael R. ;
Houk, K. N. ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (13) :4517-4526