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Iridium/Copper‐Catalyzed Oxidative C−H/O−H Annulation of Benzoic Acids with Saturated Ketones for Accessing 3‐Substituted Phthalides
Author(s) -
Wang Rui,
Xu Hongyan,
Li Tingting,
Zhang Ying,
Wang Shoufeng,
Chen Guozhu,
Li Cuncheng,
Zhao Huaiqing
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202001214
Subject(s) - annulation , chemistry , catalysis , iridium , dehydrogenation , intramolecular force , bimetallic strip , benzoic acid , organic chemistry , combinatorial chemistry , medicinal chemistry
A catalytic annulation cascade is achieved that affords an efficient access to phthalides from readily available benzoic acids and saturated ketones. The reaction is catalyzed by a bimetallic Ir/Cu system and proceeds via the combination of Cu‐catalyzed dehydrogenation of ketones and Ir‐catalyzed direct C−H functionalization under the assistance of the weakly coordinating carboxyl followed by the β−H elimination and intramolecular Michael addition. This method shows a broad scope of substrates and good functional group tolerance. The protocol furnishes an alternative strategy for the construction of diverse 3‐substituted phthalides.