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Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

2009· article· en· 973 citations· W142358202 on OpenAlex· 10.1021/ja9053338

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Abstract

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.

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The record

Venue
Journal of the American Chemical Society
Topic
Fluorine in Organic Chemistry
Field
Pharmacology, Toxicology and Pharmaceutics
Canadian institutions
Funders
National Institute of General Medical SciencesNatural Sciences and Engineering Research Council of Canada
Keywords
TrifluoromethylationChemistryEnantioselective synthesisOrganocatalysisTrifluoromethylOrganic chemistryPhotocatalysisCatalysisHalideCombinatorial chemistry
Has abstract in OpenAlex
yes