title: Three-Component Azidation of Styrene-Type Double Bonds: Light-Switchable Behavior of a Copper Photoredox Catalyst.
abstract: [Cu(dap)2]Cl effectively catalyzes azide addition from the Zhdankin reagent to styrene-type double bonds, and subsequent addition of a third component to the benzylic position. In the presence of light, a photoredox cycle is implicated with polar components such as methanol or bromide adding to a benzylic cation. In the absence of light, by contrast, double azidation takes place to give diazides. Therefore, regioselective double functionalization can be achieved in good to excellent yields, with a switch between light and dark controlling the degree of azidation.
authors.affiliation: School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL (UK).
authors.forename: Gabriele
authors.initials: G
authors.lastname: Fumagalli
authors.affiliation: School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL (UK).
authors.forename: Pauline T G
authors.initials: PT
authors.lastname: Rabet
authors.affiliation: Department of Oncology, AstraZeneca, Alderley Park, Macclesfield, SK10 4TG (UK).
authors.forename: Scott
authors.initials: S
authors.lastname: Boyd
authors.affiliation: School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL (UK). michael.greaney@manchester.ac.uk.
authors.forename: Michael F
authors.initials: MF
authors.lastname: Greaney
mesh_terms: D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D008027:Light; D010084:Oxidation-Reduction; D020058:Styrene / Q000737:chemistry*
chemical_list: D001386:Azides; D020058:Styrene; D003300:Copper
keywords: azides; copper; heterocycles; photochemistry; radicals