Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

Jacob A. Kautzky; Tao Wang; Ryan W. Evans; David W.C. Macmillan

doi:10.1021/jacs.8b02650

Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

Jacob A. Kautzky, Tao Wang, Ryan W. Evans, David W.C. Macmillan

Chemistry

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

69 Scopus citations

Abstract

Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, alcohols, and strained ring systems. To demonstrate the broad potential of this new methodology for late-stage functionalization, we successfully converted a diverse array of carboxylic acid-bearing natural products and medicinal agents to the corresponding trifluoromethyl analogues.

Original language	English (US)
Pages (from-to)	6522-6526
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	21
DOIs	https://doi.org/10.1021/jacs.8b02650
State	Published - May 30 2018

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.8b02650

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abstract = "Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, alcohols, and strained ring systems. To demonstrate the broad potential of this new methodology for late-stage functionalization, we successfully converted a diverse array of carboxylic acid-bearing natural products and medicinal agents to the corresponding trifluoromethyl analogues.",

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AU - Wang, Tao

AU - Evans, Ryan W.

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PY - 2018/5/30

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AB - Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, alcohols, and strained ring systems. To demonstrate the broad potential of this new methodology for late-stage functionalization, we successfully converted a diverse array of carboxylic acid-bearing natural products and medicinal agents to the corresponding trifluoromethyl analogues.

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