Synthesis of Stereodefined Trisubstituted Alkenyl Silanes Enabled by Borane Catalysis and Nickel Catalysis

作者:Zhang, YX (Zhang, Yunxiao)[ 1 ] ; Chen, YR (Chen, Yanran)[ 1 ] ; Zhang, ZG (Zhang, Zeguo)[ 1 ] ; Liu, SS (Liu, Shanshan)[ 1 ] ; Shen, X (Shen, Xiao)[ 1 ]

ORGANIC LETTERS

卷: 22 期: 3 页: 970-975

DOI: 10.1021/acs.orglett.9b04505

出版年: FEB 7 2020

文献类型:Article

摘要

Regioselective and stereoselective synthesis of trisubstituted alkenyl silanes via hydrosilylation is challenging. Herein, we report the first beta-anti-selective addition of silanes to thioalkynes with B(C6F5)(3) as the catalyst. The reaction shows broad substrate scope. The products were proven to be useful intermediates to other trisubstituted alkenyl silanes by Ni-catalyzed stereoretentive cross-coupling reactions of the C-S bond. A mechanism study suggests that nucleophilic attack of thioalkyne to an activated silylium intermediate might be the rate-determining step.

关键词

KeyWords Plus:S BOND-CLEAVAGE; STEREOSELECTIVE HYDROSILYLATION; 1,1-CARBOBORATION REACTIONS; SELECTIVE HYDROSILYLATION; TRANS-HYDROSILYLATION; INTERNAL THIOALKYNES; GRIGNARD-REAGENTS; ALKYNES; COMPLEX; ACTIVATION

作者信息

通讯作者地址:

Wuhan University Wuhan Univ, Engn Res Ctr Organosilicon Cpds & Mat, Inst Adv Studies, Minist Educ, 299 Bayi Rd, Wuhan 430072, Hubei, Peoples R China.

通讯作者地址: Shen, X (通讯作者)

Wuhan Univ, Engn Res Ctr Organosilicon Cpds & Mat, Inst Adv Studies, Minist Educ, 299 Bayi Rd, Wuhan 430072, Hubei, Peoples R China.

地址:

[ 1 ]‎ Wuhan Univ, Engn Res Ctr Organosilicon Cpds & Mat, Inst Adv Studies, Minist Educ, 299 Bayi Rd, Wuhan 430072, Hubei, Peoples R China

电子邮件地址:xiaoshen@whu.edu.cn