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Cobalt‐Catalyzed Intramolecular Hydroacylation Involving Cyclopropane Cleavage
Author(s) -
Yang Junfeng,
Mori Yuto,
Yamanaka Masahiro,
Yoshikai Naohiko
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001223
Subject(s) - hydroacylation , cyclopropane , intramolecular force , catalysis , chemistry , cobalt , aldehyde , olefin fiber , bond cleavage , cyclopropanation , medicinal chemistry , cleavage (geology) , ring (chemistry) , stereochemistry , photochemistry , organic chemistry , materials science , fracture (geology) , composite material
A simple cobalt‐diphosphine catalyst has been found to efficiently promote intramolecular cyclization of ortho ‐cyclopropylvinyl‐ and cyclopropylidenemethyl‐substituted benzaldehydes into benzocyclooctadienone and benzocycloheptadienone derivatives, respectively. This ring‐opening hydroacylation likely involves aldehyde C−H oxidative addition, olefin insertion, cyclopropane cleavage by β‐carbon elimination, and C−C bond‐forming reductive elimination, as was supported by mechanistic experiments and DFT calculations.