Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation To Achieve Isoquinoline Synthesis

We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranat...

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Bibliographic Details
Published in:Organic letters 2021-05, Vol.23 (10), p.4023-4028
Main Authors: Cui, Hong, Bai, Jinku, Ai, Tianyu, Zhan, Ye, Li, Guanzhong, Rao, Honghua
Format: Article
Language:English
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Summary:We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01237