A theoretical study on the ring expansion of NHCs by silanes

被引:42
作者
Iversen, Kalon J. [1 ]
Wilson, David J. D. [1 ]
Dutton, Jason L. [1 ]
机构
[1] La Trobe Univ, La Trobe Inst Mol Sci, Dept Chem, Melbourne, Vic, Australia
关键词
N-HETEROCYCLIC CARBENES; ACTIVATION; BOND;
D O I
10.1039/c3dt51503f
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A theoretical study focusing on the ring expansion that occurs in the reaction of N-heterocyclic carbenes with silanes has been carried out. A detailed reaction pathway was determined which indicates that formation of C-H bonds is the crucial factor in the transformation.
引用
收藏
页码:11035 / 11038
页数:4
相关论文
共 18 条
[1]   Preparation of Stable Low-Oxidation-State Group 14 Element Amidohydrides and Hydride-Mediated Ring-Expansion Chemistry of N-Heterocyclic Carbenes [J].
Al-Rafia, S. M. Ibrahim ;
McDonald, Robert ;
Ferguson, Michael J. ;
Rivard, Eric .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (43) :13810-13820
[2]   Efficient generation of stable adducts of Si(II) dihydride using a donor-acceptor approach [J].
Al-Rafia, S. M. Ibrahim ;
Malcolm, Adam C. ;
McDonald, Robert ;
Ferguson, Michael J. ;
Rivard, Eric .
CHEMICAL COMMUNICATIONS, 2012, 48 (09) :1308-1310
[3]   Trapping the Parent Inorganic Ethylenes H2SiGeH2 and H2SiSnH2 in the Form of Stable Adducts at Ambient Temperature [J].
Al-Rafia, S. M. Ibrahim ;
Malcolm, Adam C. ;
McDonald, Robert ;
Ferguson, Michael J. ;
Rivard, Eric .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (36) :8354-8357
[4]   Stabilization of the Heavy Methylene Analogues, GeH2 and SnH2, within the Coordination Sphere of a Transition Metal [J].
Al-Rafia, S. M. Ibrahim ;
Malcolm, Adam C. ;
Liew, Sean K. ;
Ferguson, Michael J. ;
Rivard, Eric .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (04) :777-779
[5]   Beryllium-Induced C?N Bond Activation and Ring Opening of an N-Heterocyclic Carbene [J].
Arrowsmith, Merle ;
Hill, Michael S. ;
Kociok-Koehn, Gabriele ;
MacDougall, Dugald J. ;
Mahon, Mary F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) :2098-2100
[6]   (NHCMe)SiCl4: a versatile carbene transfer reagent synthesis from silicochloroform [J].
Boettcher, Tobias ;
Bassil, Bassem S. ;
Zhechkov, Lyuben ;
Heine, Thomas ;
Roeschenthaler, Gerd-Volker .
CHEMICAL SCIENCE, 2013, 4 (01) :77-83
[7]  
Cazin CSJ, 2011, CATAL MET COMPLEXES, V32, P1, DOI 10.1007/978-90-481-2866-2
[8]  
COTTON FA, 1988, ADV INORG CHEM, P266
[9]   SiBr2(Idipp): A Stable N-Heterocyclic Carbene Adduct of Dibromosilylene [J].
Filippou, Alexander C. ;
Chernov, Oleg ;
Schnakenburg, Gregor .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5687-5690
[10]   Facile splitting of hydrogen and ammonia by nucleophilic activation at a single carbon center [J].
Frey, Guido D. ;
Lavallo, Vincent ;
Donnadieu, Bruno ;
Schoeller, Wolfgang W. ;
Bertrand, Guy .
SCIENCE, 2007, 316 (5823) :439-441