title: Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes.
abstract: Vinyl boronates react with electron-deficient alkyl iodides in the presence of visible light to give boronic esters in which two new C-C bonds have been created. The reaction occurs by radical addition of an electron-deficient alkyl radical to the vinyl boronate followed by electron transfer with another molecule of alkyl iodide, continuing the chain, and triggering a 1,2-metalate rearrangement. In a number of cases, the use of a photoredox catalyst enhances yields significantly. The scope of the radical precursor includes α-iodo ketones, esters, nitriles, primary amides, α-fluorinated halo-acetates and perfluoroalkyl iodides.
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Mattia
authors.initials: M
authors.lastname: Silvi
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Christopher
authors.initials: C
authors.lastname: Sandford
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Varinder K
authors.identifier: 0000-0003-0344-6430
authors.initials: VK
authors.lastname: Aggarwal