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Copper-catalyzed radical trans-selective hydroboration of ynamides with N-heterocyclic carbene boranes.

ABSTRACT: Vinylboron compounds are important compounds in organic chemistry and biology. In this communication, we developed a copper(I)-catalyzed, highly regio- and stereoselective radical trans-hydroboration of ynamides with N-heterocyclic carbene (NHC)-ligated borane is reported, which leads to a series of trans-boryl enmides that can be conveniently transformed into various multi-substituted enamides. Further investigation showcased that our method is robust and scalable. The mechanism of this unique reaction is studied and discussed.

SUBMITTER: Wang K

PROVIDER: S-EPMC9440302 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Copper-catalyzed radical trans-selective hydroboration of ynamides with N-heterocyclic carbene boranes.

Wang Kefeng K Yu Qingzhen Q Mao Wenli W Zheng Yuxin Y Xu Jing J Wang Yukun Y

iScience 20220817 9

Vinylboron compounds are important compounds in organic chemistry and biology. In this communication, we developed a copper(I)-catalyzed, highly regio- and stereoselective radical trans-hydroboration of ynamides with N-heterocyclic carbene (NHC)-ligated borane is reported, which leads to a series of trans-boryl enmides that can be conveniently transformed into various multi-substituted enamides. Further investigation showcased that our method is robust and scalable. The mech ...[more]

PMID: 36065185

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