Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis.
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.
Nagib
David A
DA
Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
Scott
Mark E
ME
MacMillan
David W C
DW
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D005617:Chlorofluorocarbons, Methane / Q000737:chemistry*; D008745:Methylation; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D013237:Stereoisomerism
D000447:Aldehydes; D005617:Chlorofluorocarbons, Methane; C009554:fluoroform