title: Divergent Regioselectivity in Photoredox-Catalyzed Hydrofunctionalization Reactions of Unsaturated Amides and Thioamides.
abstract: A direct method to construct 2-oxazolines and 2-thiazolines from corresponding allylic amides and thioamides is reported. The redox-neutral intramolecular hydrofunctionalization is enabled by a dual catalyst system comprised of the 9-mesityl-N-methyl acridinium tetrafluoroborate and phenyl disulphide and exhibits complete selectivity for theanti-Markovnikov regioisomeric products. The cyclization of allylic thioamides is postulated to operate via a modified mechanism in which oxidation of the thioamide, rather than the alkene, is responsible for the observed reactivity.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill Chapel Hill, NC 27599-3290, USA. Homepage: http://www.chem.unc.edu/people/faculty/nicewicz/
authors.forename: Peter D
authors.initials: PD
authors.lastname: Morse
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill Chapel Hill, NC 27599-3290, USA. Homepage: http://www.chem.unc.edu/people/faculty/nicewicz/
authors.forename: David A
authors.initials: DA
authors.lastname: Nicewicz