Rhodium(I)-Catalyzed CO-Gas-Free Arylative Dual-Carbonylation of Alkynes with Arylboronic Acids via the Formyl C-H Activation of Formaldehyde

Tsumoru Morimoto, Chuang Wang, Hiroki Tanimoto, Levent Artok, Kiyomi Kakiuchi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The rhodium(I)-catalyzed reaction of alkynes with aryl boronic acids in the presence of formaldehyde results in a CO-gas-free arylative dual-carbonylation to produce γ-butenolide derivatives. The simultaneous loading of phosphine-ligated and phosphine-free rhodium(I) complexes is required for efficient catalysis. The former complex catalyzes the abstraction of a carbonyl moiety from formaldehyde through the activation of its formyl C-H bond (decarbonylation) and the latter catalyzes the subsequent dual-incorporation of the resulting carbonyl unit (carbonylation). The use of larger amounts of the phosphine-ligated rhodium(I) complex generates more carbonyl units, leading to the formation γ-butenolides via the dual-incorporation of the carbonyl unit.

Original languageEnglish
Pages (from-to)3372-3382
Number of pages11
JournalSynthesis
Volume53
Issue number18
DOIs
StatePublished - 2021/04/22

Keywords

  • C-H activation
  • alkynes
  • arylboronic acids
  • decarbonylation
  • formaldehyde
  • rhodium
  • γ-butenolides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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