Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis

Sandrine Ventre; Filip R. Petronijevic; David W.C. Macmillan

doi:10.1021/jacs.5b02244

Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis

Sandrine Ventre
, Filip R. Petronijevic
, David W.C. Macmillan

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

351 Scopus citations

Abstract

The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO₂-extrusion and F^• transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

Original language	English (US)
Pages (from-to)	5654-5657
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	17
DOIs	https://doi.org/10.1021/jacs.5b02244
State	Published - May 6 2015

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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title = "Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis",

abstract = "The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F• transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.",

author = "Sandrine Ventre and Petronijevic, \{Filip R.\} and Macmillan, \{David W.C.\}",

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AU - Petronijevic, Filip R.

AU - Macmillan, David W.C.

PY - 2015/5/6

Y1 - 2015/5/6

N2 - The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F• transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

AB - The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F• transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

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UR - https://www.scopus.com/pages/publications/84928963782#tab=citedBy

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JF - Journal of the American Chemical Society

IS - 17

ER -

Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis

Abstract

All Science Journal Classification (ASJC) codes

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