title: Visible-Light-Mediated Alkenylation, Allylation, and Cyanation of Potassium Alkyltrifluoroborates with Organic Photoredox Catalysts.
abstract: Iridium- and ruthenium-free approaches to protected allylic amines and alkyl nitriles under photoredox conditions are reported. An inexpensive organic dye, eosin Y, catalyzes coupling of Boc-protected potassium α-aminomethyltrifluoroborates with a variety of substituted alkenyl sulfones through an α-aminomethyl radical addition-elimination pathway. Allylic and homoallylic amines were formed in moderate yields with high E/Z selectivity. The mechanistic approach was extended using tosyl cyanide as a radical trap, enabling the conversion of alkyltrifluoroborates to nitriles via a Fukuzumi acridinium-catalyzed process.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Drew R
authors.initials: DR
authors.lastname: Heitz
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Komal
authors.initials: K
authors.lastname: Rizwan
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D008027:Light; D009930:Organic Chemicals / Q000737:chemistry*; D010084:Oxidation-Reduction; D017680:Potassium Compounds / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000475:Alkenes; D001896:Boron Compounds; D003486:Cyanides; D009930:Organic Chemicals; D017680:Potassium Compounds