Visible‐Light‐Driven Regioselective Di‐ and Tri‐fluoromethylative Benzylation Reaction of 1,1‐Diphenylethylenes

Herein, we report a facile methodology for a visible light-induced three-component regioselective di- and tri-fluoromethylative benzylation reaction of 1,1-diphenylethylenes via the deamination of benzylamines. The key step of this approach is the formation of an electron donor-acceptor (EDA) complex between sodium di/tri-fluoromethanesulfinate and the Katritzky salt. Subsequently, a single electron transfer occurs within the EDA complex, generating di/tri fluoromethyl and benzyl radicals, which results in the formation of valuable quaternary carbon-containing di/trifluoromethylated molecules in a single step. By strategically choosing di/trifluoromethyl as a transient radical over the benzyl radical, a regioselective three-component radical-radical cross-coupling reaction has been achieved. Mechanistic investigations suggest that the reaction proceeds via a radical pathway.

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Publication Details

Journal
Chemistry - A European Journal
Published
2026-04-17
DOI
https://doi.org/10.1002/chem.71021
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Visible‐Light‐Driven Regioselective Di‐ and Tri‐fluoromethylative Benzylation Reaction of 1,1‐Diphenylethylenes

K. Keerthika, Apurba Kumar Pal, S. Srividya, K Geetharani
Chemistry - A European Journal
Radical Photochemical Reactions
article

Visible‐Light‐Driven Regioselective Di‐ and Tri‐fluoromethylative Benzylation Reaction of 1,1‐Diphenylethylenes

K. Keerthika, Apurba Kumar Pal, S. Srividya, K Geetharani
article en

Abstract

Herein, we report a facile methodology for a visible light-induced three-component regioselective di- and tri-fluoromethylative benzylation reaction of 1,1-diphenylethylenes via the deamination of benzylamines. The key step of this approach is the formation of an electron donor-acceptor (EDA) complex between sodium di/tri-fluoromethanesulfinate and the Katritzky salt. Subsequently, a single electron transfer occurs within the EDA complex, generating di/tri fluoromethyl and benzyl radicals, which results in the formation of valuable quaternary carbon-containing di/trifluoromethylated molecules in a single step. By strategically choosing di/trifluoromethyl as a transient radical over the benzyl radical, a regioselective three-component radical-radical cross-coupling reaction has been achieved. Mechanistic investigations suggest that the reaction proceeds via a radical pathway.

Chemistry - A European Journal
Indian Institute of Science Bangalore (IN)
Council of Scientific and Industrial Research, India
Clean water and sanitation
Openalex Percentile: Top 11%
Radical Photochemical Reactions
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