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Open AccessArticle

PPh3-Assisted Esterification of Acyl Fluorides with Ethers via C(sp3)–O Bond Cleavage Accelerated by TBAT

1
Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan
2
Research Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan
*
Author to whom correspondence should be addressed.
Catalysts 2019, 9(7), 574; https://doi.org/10.3390/catal9070574
Received: 23 May 2019 / Revised: 21 June 2019 / Accepted: 26 June 2019 / Published: 28 June 2019
(This article belongs to the Special Issue Catalysis and Fine Chemicals)
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. View Full-Text
Keywords: Acyl fluorides; cyclopentyl methyl ether (CPME); tetrabutylammonium difluorotriphenysilicate (TBAT); carbon-oxygen bond cleavage; esterification Acyl fluorides; cyclopentyl methyl ether (CPME); tetrabutylammonium difluorotriphenysilicate (TBAT); carbon-oxygen bond cleavage; esterification
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MDPI and ACS Style

Wang, Z.; Wang, X.; Nishihara, Y. PPh3-Assisted Esterification of Acyl Fluorides with Ethers via C(sp3)–O Bond Cleavage Accelerated by TBAT. Catalysts 2019, 9, 574.

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