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

Zhenhua Wang; Xiu Wang; Yasushi Nishihara

doi:10.3390/catal9070574

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

Zhenhua Wang, Xiu Wang, Yasushi Nishihara

Research Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

11 Citations (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 language	English
Article number	574
Journal	Catalysts
Volume	9
Issue number	7
DOIs	https://doi.org/10.3390/catal9070574
Publication status	Published - Jul 2019

Keywords

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

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry

Access to Document

10.3390/catal9070574

Cite this

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

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.",

keywords = "Acyl fluorides, Carbon-oxygen bond cleavage, Cyclopentyl methyl ether (CPME), Esterification, Tetrabutylammonium difluorotriphenysilicate (TBAT)",

author = "Zhenhua Wang and Xiu Wang and Yasushi Nishihara",

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year = "2019",

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language = "English",

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T1 - PPh3-assisted esterification of acyl fluorides with ethers via C(Sp3 )–O bond cleavage accelerated by TBAT

AU - Wang, Zhenhua

AU - Wang, Xiu

AU - Nishihara, Yasushi

PY - 2019/7

Y1 - 2019/7

N2 - 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.

AB - 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.

KW - Acyl fluorides

KW - Carbon-oxygen bond cleavage

KW - Cyclopentyl methyl ether (CPME)

KW - Esterification

KW - Tetrabutylammonium difluorotriphenysilicate (TBAT)

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