Cobalt-Catalyzed Z-Selective Hydrosilylation of Terminal Alkynes

被引:130
作者
Teo, Wei Jie [1 ]
Wang, Chao [1 ]
Tan, Ye Wei [1 ]
Ge, Shaozhong [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore
关键词
alkynes; cobalt; homogeneous catalysis; hydrosilylation; vinylsilanes; STEREOSELECTIVE HYDROSILYLATION; ALKENE HYDROSILYLATION; RUTHENIUM COMPLEX; HYDROBORATION; REGIO; MECHANISM; ISOMERIZATION; HYDROSILATION; EFFICIENT; RHODIUM;
D O I
10.1002/anie.201700868
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A cobalt-catalyzed Z-selective hydrosilylation of alkynes has been developed relying on catalysts generated from bench-stable Co(OAc)(2) and pyridine-2,6-diimine (PDI) ligands. A variety of functionalized aromatic and aliphatic alkynes undergo this transformation, yielding Z-vinylsilanes in high yields with excellent selectivities (Z/E ratio ranges from 90: 10 to >99: 1). The addition of a catalytic amount of phenol effectively suppressed the Z/E-isomerization of the Z-vinylsilanes that formed under catalytic conditions.
引用
收藏
页码:4328 / 4332
页数:5
相关论文
共 51 条
[1]  
[Anonymous], 15293203 CCDC
[2]  
[Anonymous], 2013, ANGEW CHE
[3]  
[Anonymous], 2016, Angew. Chem, DOI DOI 10.1002/ANGE.201605501
[4]   Bis(imino)pyridine Cobalt-Catalyzed Dehydrogenative Silylation of Alkenes: Scope, Mechanism, and Origins of Selective Allylsilane Formation [J].
Atienza, Crisita Carmen Hojilla ;
Diao, Tianning ;
Weller, Keith J. ;
Nye, Susan A. ;
Lewis, Kenrick M. ;
Delis, Johannes G. P. ;
Boyer, Julie L. ;
Roy, Aroop K. ;
Chirik, Paul J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (34) :12108-12118
[5]   MECHANISM OF A COBALT(III)-CATALYZED OLEFIN HYDROSILATION REACTION - DIRECT EVIDENCE FOR A SILYL MIGRATION PATHWAY [J].
BROOKHART, M ;
GRANT, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (06) :2151-2156
[6]   Amine-Activated Iron Catalysis: Air- and Moisture-Stable Alkene and Alkyne Hydrofunctionalization [J].
Challinor, Amy J. ;
Calin, Marc ;
Nichol, Gary S. ;
Carter, Neil B. ;
Thomas, Stephen P. .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (15) :2404-2409
[7]   Rapid, Regioconvergent, Solvent-Free Alkene Hydrosilylation with a Cobalt Catalyst [J].
Chen, Chi ;
Hecht, Maxwell B. ;
Kavara, Aydin ;
Brennessel, William W. ;
Mercado, Brandon Q. ;
Weix, Daniel J. ;
Holland, Patrick L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (41) :13244-13247
[8]   Z-Selective Alkene Isomerization by High-Spin Cobalt(II) Complexes [J].
Chen, Chi ;
Dugan, Thomas R. ;
Brennessel, William W. ;
Weix, Daniel J. ;
Holland, Patrick L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :945-955
[9]   A theoretical study on the mechanism, regiochemistry, and stereochemistry of hydrosilylation catalyzed by cationic ruthenium complexes [J].
Chung, LW ;
Wu, YD ;
Trost, BM ;
Ball, ZT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11578-11582
[10]   Highly stereoselective hydrocarbation of terminal alkynes via Pt-catalyzed hydrosilylation/Pd-catalyzed cross-coupling reactions [J].
Denmark, SE ;
Wang, ZG .
ORGANIC LETTERS, 2001, 3 (07) :1073-1076