4.8 Article

Photoinduced Defluorinative Branch-Selective Olefination of Multifluoro (Hetero)arenes

Journal

ORGANIC LETTERS
Volume 25, Issue 5, Pages 883-888

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c00115

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We have developed a photoredox platform that utilizes sulfinate as a radical-relay precursor and a sacrificial nucleofuge, allowing for the construction of styrenyl polyfluoro (hetero)arenes with branch selectivity. This protocol combines photoredox catalysis, radical-radical coupling, and an elimination process in a one-pot operation, providing a mild and efficient method to access polyfluoro (hetero)aryl derivatives of natural products and drugs.
We report a photoredox platform for constructing styrenyl polyfluoro (hetero)arenes with branch selectivity by taking advantage of sulfinate as both a radical-relay precursor and a sacrificial nucleofuge. This protocol merges photoredox catalysis with radical-radical coupling and an elimination process in a one-pot operation and features good functional group tolerance, mild conditions, and a facile method to access polyfluoro (hetero)aryl derivatives of natural products and drugs.

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