PPh3-assisted esterification of acyl fluorides with ethers via C(Sp3 )–O bond cleavage accelerated by TBAT

Zhenhua Wang, Xiu Wang, Yasushi Nishihara

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

We describe the (triphenylphosphine (PPh3)-assisted methoxylation of acyl fluorides with cyclopentyl methyl ether (CPME) accelerated by tetrabutylammonium difluorotriphenysilicate (TBAT) via regiospecific C–OMe bond cleavage. Easily available CPME is utilized not only as the solvent, but a methoxylating agent in this transformation. The present method is featured by C–O and C–F bond cleavage under metal-free conditions, good functional-group tolerance, and wide substrate scope. Mechanistic studies revealed that the radical process was not involved.

Original languageEnglish
Article number574
JournalCatalysts
Volume9
Issue number7
DOIs
Publication statusPublished - Jul 1 2019

Fingerprint

Methyl Ethers
Ethers
Esterification
Fluorides
fluorides
cleavage
ethers
Carbon Monoxide
Functional groups
Metals
Substrates
metals
tetrabutylammonium
triphenylphosphine

Keywords

  • Acyl fluorides
  • Carbon-oxygen bond cleavage
  • Cyclopentyl methyl ether (CPME)
  • Esterification
  • Tetrabutylammonium difluorotriphenysilicate (TBAT)

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Cite this

PPh3-assisted esterification of acyl fluorides with ethers via C(Sp3 )–O bond cleavage accelerated by TBAT. / Wang, Zhenhua; Wang, Xiu; Nishihara, Yasushi.

In: Catalysts, Vol. 9, No. 7, 574, 01.07.2019.

Research output: Contribution to journalArticle

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