Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes

Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes
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镍催化乙烯基芳烃的对映选择性硼氢化

DOI:
10.1021/acs.orglett.1c04073
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发表时间:
2022
期刊:
影响因子:
5.2
通讯作者:
Stanley, Levi M.
Stanley, Levi M.
中科院分区:
化学1区
文献类型:
--
作者:
Tran, Hai N.;Stanley, Levi M.

文献摘要

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介绍了一种手性非外消旋镍催化剂催化乙烯基芳烃硼氢化反应生成手性苄基硼酸酯的简便方法。各种乙烯基芳烃与双(频哪醇合)二硼(B2pin2)在MeOH作为氢化物源的存在下反应,以高达92%的产率和高达94%ee形成手性硼酸酯。使用无水Me4NF活化B2pin2对于确保快速金属转移以实现高对映选择性至关重要。
The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2is crucial for ensuring fast transmetalation to achieve high enantioselectivities.