Divergent ring-opening coupling between cyclopropanols and alkynes under cobalt catalysis

Junfeng Yang, Yixiao Shen, Yang Jie Lim, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

Cobalt-diphosphine catalysts promote ring-opening coupling reactions between cyclopropanols and unactivated internal alkynes, affording either β-alkenyl ketones or multisubstituted cyclopentenol derivatives in good yields with good to excellent regioselectivities. The chemoselectivity between these β-alkenylation and [3 + 2] annulation reactions, which likely share a cobalt homoenolate as a key catalytic intermediate, is exquisitely controlled by the reaction conditions, with the solvent being a major controlling factor. The reactions are proposed to involve ring opening of cobalt cyclopropoxide into homoenolate, migratory insertion of the alkyne into the Co-C bond, and protodemetalation or intramolecular carbonyl addition of the resulting alkenylcobalt species. The feasibility of these reaction steps was supported by DFT calculations.

Original languageEnglish
Pages (from-to)6928-6934
Number of pages7
JournalChemical Science
Volume9
Issue number34
DOIs
Publication statusPublished - 2018
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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