Cobalt-Catalyzed Arylative Cyclization of Acetylenic Esters and Ketones with Arylzinc Reagents through 1,4-Cobalt Migration

Jianming Yan, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

1,4-Migrations of organopalladium and organorhodium species have been utilized for the development of various cascade reactions involving remote C-H bond activation. Recently, we reported a cobalt-catalyzed migratory arylzincation reaction of an alkyne that features alkenyl-to-aryl 1,4-cobalt migration and cobalt-to-zinc transmetalation as key steps. We report herein that the cobalt/arylzinc combination can also promote a cascade arylative cyclization reaction of alkynes bearing pendant ester or ketone moieties to afford benzo-fused cyclic ketone or alcohol products, respectively. The reaction is considered to proceed through insertion of the alkyne into an arylcobalt species, 1,4-cobalt migration, and intramolecular organocobalt addition to the carbonyl group. The present cobalt/arylzinc system may not only serve as an alternative to previously reported rhodium/arylboron and iridium/arylboron systems but also complement their scopes in the arylative cyclization.

Original languageEnglish
Pages (from-to)3738-3742
Number of pages5
JournalACS Catalysis
Volume6
Issue number6
DOIs
Publication statusPublished - 2016 Jun 3
Externally publishedYes

Keywords

  • C-H activation
  • alkynes
  • cascade reactions
  • cobalt
  • organozinc reagents

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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