Visible-Light-Driven Regioselective Di- and Tri-fluoromethylative Benzylation Reaction of 1,1-Diphenylethylenes
K Keerthika1, S Srividya1, Apurba Kumar Pal1
1Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bengaluru, India.
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.
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