The Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

By David A. Nagib, Mark E. Scott, D. MacMillan. Journal of the American Chemical Society, 2009

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The first enantioselective, organocatalytic alpha-trifluoromethylation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

Subfields: Organic Chemistry, Pharmaceutical Science

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