Gold-Mediated C-I Bond Activation of Iodobenzene

被引:82
作者
Robinson, Peter S. D. [1 ,2 ]
Khairallah, George N. [1 ,2 ]
da Silva, Gabriel [3 ]
Lioe, Hadi [1 ,2 ]
O'Hair, Richard A. J. [1 ,2 ]
机构
[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia
[2] Univ Melbourne, Inst Mol Sci & Biotechnol Bio21, Melbourne, Vic 3010, Australia
[3] Univ Melbourne, Dept Chem & Biomol Engn, Melbourne, Vic 3010, Australia
基金
澳大利亚研究理事会;
关键词
bond activation; density functional calculations; gas-phase reactions; gold; mass spectrometry; GAS-PHASE SYNTHESIS; SONOGASHIRA REACTION; METAL-IONS; CATALYSTS; PHENYLACETYLENE; NANOPARTICLES; ALKANES; SITE;
D O I
10.1002/anie.201108502
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Controversy resolved! A combination of gas-phase ion-molecule reactions and theoretical studies confirm bisligated mononuclear Au I complexes are unable to undergo oxidative addition of iodobenzene for Sonogashira coupling, but that the ligated gold clusters [Au 3L n] + (L=Ph 2P(CH 2) nPPh 2; n=3-6) activate the C-I bond. DFT calculations on the transition states show that the linker size n tunes the cluster reactivity. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:3812 / 3817
页数:6
相关论文
共 41 条
[11]   Resolving Heterogeneity Problems and Impurity Artifacts in Operationally Homogeneous Transition Metal Catalysts [J].
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2012, 112 (03) :1536-1554
[12]   Copper-free Sonogashira reaction using gold nanoparticles supported on Ce2O3, Nb2O5 and SiO2 under microwave irradiation [J].
de Souza, Rodrigo O. M. A. ;
Bittar, Mariana S. ;
Mendes, Laiza V. P. ;
da Silva, Carla Michele F. ;
da Silva, Victor Teixeira ;
Antunes, O. A. C. .
SYNLETT, 2008, (12) :1777-1780
[13]  
Donald W.A., 2011, Angew. Chem, V123, P8529
[14]   C-H Bond Activation of Methanol and Ethanol by a High-Spin FeIVO Biomimetic Complex [J].
Donald, William A. ;
McKenzie, Christine J. ;
O'Hair, Richard A. J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (36) :8379-8383
[15]   REACTIONS OF MONOSUBSTITUTED ALKANES WITH BARE METAL-IONS - AN EFFORT TOWARD A MORE UNIFIED PICTURE FOR THE GAS-PHASE CHEMISTRY OF R-X MOLECULES [J].
ELLER, K .
COORDINATION CHEMISTRY REVIEWS, 1993, 126 (1-2) :93-147
[16]   Bite angle effects in diphosphine metal catalysts: steric or electronic? [J].
Freixa, Z ;
van Leeuwen, PWNM .
DALTON TRANSACTIONS, 2003, (10) :1890-1901
[17]  
Frisch M. J., 2016, Gaussian 03 Revision B.03
[18]   Impact of swapping ethyl for phenyl groups on diphosphine-protected undecagold [J].
Golightly, Justin S. ;
Gao, Lin ;
Castleman, A. Welford, Jr. ;
Bergeron, Denis E. ;
Hudgens, Jeffrey W. ;
Magyar, Rudolph J. ;
Gonzalez, Carlos A. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2007, 111 (40) :14625-14627
[19]   Catalysis by gold(I) and gold(III):: A parallelism between homo- and heterogeneous catalysts for copper-free Sonogashira cross-coupling reactions [J].
Gonzalez-Arellano, Camino ;
Abad, Alberto ;
Corma, Avelino ;
Garcia, Hermenegildo ;
Iglesias, Marta ;
Sanchez, Felix .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1536-1538
[20]   Toward an Understanding of Ligand Selectivity in Nanocluster Synthesis [J].
Hong, Sampyo ;
Shafai, Ghazal ;
Bertino, Massimo ;
Rahman, Talat S. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2011, 115 (30) :14478-14487