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Rh‐Catalyzed Reaction of Propargylic Alcohols with Aryl Boronic Acids–Switch from β‐OH Elimination to Protodemetalation
Author(s) -
Wang Weiyi,
Qian Hui,
Ma Shengming
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000044
Subject(s) - chemistry , stereoselectivity , regioselectivity , reagent , racemization , aryl , catalysis , combinatorial chemistry , organic chemistry , alcohol , reaction conditions , alkyl
Summary of main observation and conclusion It is known that Rh‐catalyzed reaction of propargylic alcohols with aryl metallic reagents undergoes S N 2’‐type reaction affording allenes via a sequential arylmetalation and β‐OH elimination process. Here we report a Rh/Ag‐cocatalyzed reaction of propargylic alcohols with organoboronic acids affording stereo‐defined ( E )‐3‐arylallylic alcohols via arylmetalation and protodemetalation with a high regio‐ and stereoselectivity under very mild conditions. The reaction exhibits a good substrate scope and the compatibility with synthetically useful functional groups with no racemization for optically active propargylic alcohols. Such a reaction may also be extended to homopropargylic alcohols with a remarkable regioselectivity and exclusive E ‐stereoselectivity.