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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K. Keerthika
S. Srividya
Apurba Kumar Pal
Chemistry - A European Journal
Indian Institute of Science Bangalore
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Keerthika et al. (Fri,) studied this question.
www.synapsesocial.com/papers/69e5c36103c293991402923b — DOI: https://doi.org/10.1002/chem.71021