title: Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis.
abstract: Halofunctionalization of alkenes is a classical method for olefin difunctionalization. It gives rise to adducts which are found in many natural products and biologically active molecules, and offers a synthetic handle for further manipulation. Classically, this reaction is performed with an electrophilic halogen source and leads to regioselective formation of the halofunctionalized adducts. Herein, we demonstrate a reversal of the native regioselectivity for alkene halofunctionalization through the use of an acridinium photooxidant in conjunction with a copper cocatalyst.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599-3290, USA.
authors.forename: Jeremy D
authors.initials: JD
authors.lastname: Griffin
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599-3290, USA.
authors.forename: Cortney L
authors.initials: CL
authors.lastname: Cavanaugh
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599-3290, USA.
authors.forename: David A
authors.initials: DA
authors.lastname: Nicewicz
mesh_terms: D000166:Acridines / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D010083:Oxidants, Photochemical / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000166:Acridines; D000475:Alkenes; D010083:Oxidants, Photochemical; D003300:Copper
keywords: cooperative catalysis; halofunctionalization; organocatalysis; photoredox catalysis; radicals