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Synthesis of Stereodefined Trisubstituted Alkenyl Silanes Enabled by Borane Catalysis and Nickel Catalysis.
Organic Letters ( IF 4.9 ) Pub Date : 2020-01-24 , DOI: 10.1021/acs.orglett.9b04505
Yunxiao Zhang 1 , Yanran Chen 1 , Zeguo Zhang 1 , Shanshan Liu 1 , Xiao Shen 1
Affiliation  

Regioselective and stereoselective synthesis of trisubstituted alkenyl silanes via hydrosilylation is challenging. Herein, we report the first β-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.

中文翻译:

硼烷催化和镍催化实现立体定义的三取代烯基硅烷的合成。

通过氢化硅烷化的三取代烯基硅烷的区域选择性和立体选择性合成是具有挑战性的。本文中,我们报道了以B(C6F5)3为催化剂向硫代炔烃中的硅烷的第一个β-抗选择性加成反应。反应显示出广泛的底物范围。通过CS键的Ni催化的立体保持性交叉偶联反应,证明该产物是其他三取代的烯基硅烷的有用中间体。一项机理研究表明,硫代炔对活化的甲硅烷基中间体的亲核攻击可能是决定速率的步骤。
更新日期:2020-01-26
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