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
[41]   SOLVENT-CONTROLLED STEREOSELECTIVITY IN THE HYDROSILYLATION OF ALK-1-YNES CATALYZED BY RHODIUM COMPLEXES [J].
TAKEUCHI, R ;
TANOUCHI, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (20) :2909-2913
[42]   UNUSUAL ACTIVITY AND SELECTIVITY IN ALKYNE HYDROSILYLATION WITH AN IRIDIUM CATALYST STABILIZED BY AN O-DONOR LIGAND [J].
TANKE, RS ;
CRABTREE, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :7984-7989
[43]   Alkyne Semihydrogenation with a Well-Defined Nonclassical Co-H2 Catalyst: A H2 Spin on Isomerization and E-Selectivity [J].
Tokmic, Kenan ;
Fout, Alison R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (41) :13700-13705
[44]   Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: Efficient and general trans addition [J].
Trost, BM ;
Ball, ZT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17644-17655
[45]   Cobalt-Catalyzed Regiodivergent Hydrosilylation of Vinylarenes and Aliphatic Alkenes: Ligand- and Silane-Dependent Regioselectivities [J].
Wang, Chao ;
Teo, Wei Jie ;
Ge, Shaozhong .
ACS CATALYSIS, 2017, 7 (01) :855-863
[46]   Dual-Stereocontrol Asymmetric Cobalt-Catalyzed Hydroboration of Sterically Hindered Styrenes [J].
Zhang, Heyi ;
Lu, Zhan .
ACS CATALYSIS, 2016, 6 (10) :6596-6600
[47]   Synthesis of 1,1,1-Tris(boronates) from Vinylarenes by Co-Catalyzed Dehydrogenative Borylations-Hydroboration [J].
Zhang, Lei ;
Huang, Zheng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (50) :15600-15603
[48]   Cobalt-Catalyzed Enantioselective Hydroboration of 1,1-Disubstituted Aryl Alkenes [J].
Zhang, Lei ;
Zuo, Ziqing ;
Wan, Xiaolong ;
Huang, Zheng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) :15501-15504
[49]   A Cobalt-Catalyzed Alkene Hydroboration with Pinacolborane [J].
Zhang, Lei ;
Zuo, Ziqing ;
Leng, Xuebing ;
Huang, Zheng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (10) :2696-2700
[50]  
Zuo Z., 2016, Angew. Chem. Int. Ed, V128, P10997