Cobalt-Catalyzed Intramolecular Hydroacylation Involving Cyclopropane Cleavage

Junfeng Yang, Yuto Mori, Masahiro Yamanaka, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8302-8307
Number of pages6
JournalChemistry - A European Journal
Volume26
Issue number37
DOIs
Publication statusPublished - 2020 Jul 2
Externally publishedYes

Keywords

  • C−C bond cleavage
  • C−H activation
  • cobalt
  • cyclopropanes
  • hydroacylation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Cobalt-Catalyzed Intramolecular Hydroacylation Involving Cyclopropane Cleavage'. Together they form a unique fingerprint.

Cite this