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Direct Access to Acyl Fluorides from Carboxylic Acids Using a Phosphine/Fluoride Deoxyfluorination Reagent System

Socrates B. Munoz, Huong Dang, Xanath Ispizua-Rodriguez, Thomas Mathew, G. K. Surya Prakash*

*Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, United States, Email: gprakashusc.edu

S. B. Munoz, H. Dang, X. Ispizua-Rodriguez, T. Mathew, G. K. S. Prakash, Org. Lett., 2019, 21, 1659-1663.

DOI: 10.1021/acs.orglett.9b00197 (free Supporting Information)


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Abstract

A fast and simple method for deoxyfluorination of carboxylic acids employs commodity chemicals (PPh3, NBS, fluoride) to afford products in excellent yields under mild conditions. The protocol offers scalability, high functional group tolerance, chemoselectivity, and easy purification of products.

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Key Words

acyl fluorides


ID: J54-Y2019