Highly Chemo-, Regio-, and Stereoselective Cobalt-Catalyzed Markovnikov Hydrosilylation of Alkynes

被引：168

作者：

Guo, Jun ^{[1
]}

Lu, Zhan ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310058, Zhejiang, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 36期

关键词：

alkynes; cobalt catalysis; homogeneous catalysis; hydroboration; hydrosilylation; TERTIARY BORONIC ESTERS; ASYMMETRIC ALKENE HYDROGENATION; SILICON-CONTAINING COMPOUNDS; ORGANIC-SYNTHESIS; TERMINAL ALKYNES; ORGANOSILICON COMPOUNDS; RUTHENIUM COMPLEXES; SECONDARY ALCOHOLS; ARYL ALKENES; HYDROBORATION;

D O I：

10.1002/anie.201605501

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly chemo-, regio- and stereoselective cobalt-catalyzed Markovnikov hydrosilylation of alkynes was developed. Various functionalized groups, such as halides, free alcohols, free aniline, ketones, esters, amides, and nitriles are tolerated, which may lead to further applications and late-stage derivatizations. To date, this is the most efficient cobalt catalytic system (TOF=65520h(-1); TOF=turnover frequency) for hydrosilylation of alkynes. The Hiyama-Denmark cross-coupling reactions of vinylsilanes with aryl iodides underwent smoothly to afford 1,1-diarylethenes. A unique regioselectivity-controllable hydrosilylation/hydroboration reaction of alkynes was also described.

引用

页码：10835 / 10838

页数：4

共 73 条

[61] Diversity-Oriented Synthesis of Disubstituted Alkenes Using Masked Silanols [J].

Sore, Hannah F. ;

Blackwell, David T. ;

MacDonald, Simon J. F. ;

Spring, David R. .

ORGANIC LETTERS, 2010, 12 (12) :2806-2809

[62] Enantiodivergent conversion of chiral secondary alcohols into tertiary alcohols [J].

Stymiest, Jake L. ;

Bagutski, Viktor ;

French, Rosalind M. ;

Aggarwal, Varinder K. .

NATURE, 2008, 456 (7223) :778-U61

[63] Cobalt Complex-Catalyzed Hydrosilylation of Alkenes and Alkynes [J].

Sun, Jian ;

Deng, Liang .

ACS CATALYSIS, 2016, 6 (01) :290-300

[64] Regioselective hydrosilylation of terminal acetylenes via acetylene-Co2(CO)4dppm complex:: effects of the ligands in acetylenedicobalt complex [J].

Tojo, S ;

Isobe, M .

TETRAHEDRON LETTERS, 2005, 46 (03) :381-384

[65] 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

[66] Markovnikov alkyne hydrosilylation catalyzed by ruthenium complexes [J].

Trost, BM ;

Ball, ZT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) :12726-12727

[67] Copper-Catalyzed Highly Regioselective Silylcupration of Terminal Alkynes to Form α-Vinylsilanes [J].

Wang, Peng ;

Yeo, Xue-Liang ;

Loh, Teck-Peng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) :1254-1256

[68] Palladium-Catalyzed C-2 C-H Heteroarylation of Chiral Oxazolines: Diverse Synthesis of Chiral Oxazoline Ligands [J].

Xi, Tuo ;

Mei, Yuncai ;

Lu, Zhan .

ORGANIC LETTERS, 2015, 17 (24) :5939-5941

[69] Stereodivergent formation of alkenylsilanes:: syn or anti hydrosilylation of alkynes catalyzed by a cyclopentadienylcobalt(I) chelate bearing a pendant phosphane tether [J].

Yong, Li ;

Kirleis, Karin ;

Butenschoen, Holger .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) :833-836

[70]

Zhang G., 2012, Angew. Chem, V124, P12268, DOI DOI 10.1002/ANGE.201206051

← 1 2 3 4 5 6 7 8 →