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      Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

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          Abstract

          The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single‐electron reduction of an α‐boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α‐amino, α‐oxy, and alkyl carboxylic acids, thus providing a novel method to rapidly access boron‐containing molecules of potential biological importance.

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          Author and article information

          Contributors
          v.aggarwal@bristol.ac.uk
          Journal
          Angew Chem Int Ed Engl
          Angew. Chem. Int. Ed. Engl
          10.1002/(ISSN)1521-3773
          ANIE
          Angewandte Chemie (International Ed. in English)
          John Wiley and Sons Inc. (Hoboken )
          1433-7851
          1521-3773
          26 January 2018
          19 February 2018
          : 57
          : 8 ( doiID: 10.1002/anie.v57.8 )
          : 2155-2159
          Affiliations
          [ 1 ] School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS UK
          Author notes
          [†]

          These authors contributed equally to this work.

          Author information
          http://orcid.org/0000-0001-9203-7828
          http://orcid.org/0000-0001-7293-5014
          http://orcid.org/0000-0001-7742-4934
          http://orcid.org/0000-0003-0344-6430
          Article
          ANIE201712186
          10.1002/anie.201712186
          5838549
          29316095
          65954102-01b9-48d8-bd91-e201d34a51d3
          © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

          This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

          History
          : 28 November 2017
          Page count
          Figures: 7, Tables: 4, References: 64, Pages: 5, Words: 0
          Funding
          Funded by: Engineering and Physical Sciences Research Council
          Award ID: EP/I038071/1
          Funded by: H2020 European Research Council
          Award ID: 670668
          Funded by: Deutsche Forschungsgemeinschaft
          Categories
          Communication
          Communications
          Photochemistry
          Custom metadata
          2.0
          anie201712186
          February 19, 2018
          Converter:WILEY_ML3GV2_TO_NLMPMC version:version=5.3.2.2 mode:remove_FC converted:06.03.2018

          Chemistry
          amino acids,boron,photochemistry,radical reactions,reaction mechanisms
          Chemistry
          amino acids, boron, photochemistry, radical reactions, reaction mechanisms

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