Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

David A. Nagib, Mark E. Scott and David W. C. MacMillan*

*Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, Email: dmacmillprinceton.edu

D. A. Nagib, M. E. Scott, D. W. C. MacMillan, J. Am. Chem. Soc., 2009, 131, 10875-10877.

DOI: 10.1021/ja9053338

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Abstract

An organocatalytic α-trifluoromethylation and α-perfluoroalkylation of aldehydes with commercially available perfluoroalkyl halides in the presence of a readily available iridium photocatalyst and a chiral imidazolidinone catalyst delivers products with high efficiency and enantioselectivity. α-Trifluoromethyl aldehydes are versatile precursors for the construction of enantioenriched trifluoromethylated building blocks.

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Key Words

α-trifluoromethyl carbonyl compounds, β-trifluoromethyl alcohols

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ID: J48-Y2009