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      Concerted Nucleophilic Aromatic Substitution Reactions

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          Abstract

          Recent developments in experimental and computational chemistry have identified a rapidly growing class of nucleophilic aromatic substitutions that proceed by concerted (cS NAr) rather than classical, two‐step, S NAr mechanisms. Whereas traditional S NAr reactions require substantial activation of the aromatic ring by electron‐withdrawing substituents, such activating groups are not mandatory in the concerted pathways.

          Abstract

          Concerted or stepwise? A class of nucleophilic aromatic substitutions has been developed that proceeds by concerted (cS NAr) rather than classical, two‐step, S NAr mechanisms. Whereas traditional S NAr reactions require substantial activation of the aromatic ring by electron‐withdrawing substituents, such activating groups are not mandatory in the concerted pathways.

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          Author and article information

          Contributors
          tell.tuttle@strath.ac.uk
          shunsuke@ntu.edu.sg
          john.murphy@strath.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
          13 September 2019
          11 November 2019
          : 58
          : 46 ( doiID: 10.1002/anie.v58.46 )
          : 16368-16388
          Affiliations
          [ 1 ] Department of Pure and Applied Chemistry University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UK
          [ 2 ] Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
          [ 3 ] GlaxoSmithKline Medicines Research Centre Gunnels Wood Road Stevenage SG1 2NY UK
          Author notes
          [†]

          These authors contributed equally.

          Author information
          http://orcid.org/0000-0003-2300-8921
          http://orcid.org/0000-0003-2039-023X
          http://orcid.org/0000-0003-3136-0845
          Article
          ANIE201902216
          10.1002/anie.201902216
          6899550
          30990931
          0b1cf85c-3ef0-4679-97dd-adeb8818dd1f
          © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

          This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

          History
          : 19 February 2019
          : 11 April 2019
          Page count
          Figures: 55, Tables: 1, References: 122, Pages: 21, Words: 0
          Funding
          Funded by: GlaxoSmithKline , open-funder-registry 10.13039/100004330;
          Funded by: University of Strathclyde , open-funder-registry 10.13039/100008078;
          Categories
          Review
          Reviews
          Nucleophilic Aromatic Substitution
          Custom metadata
          2.0
          November 11, 2019
          Converter:WILEY_ML3GV2_TO_JATSPMC version:5.7.2 mode:remove_FC converted:05.12.2019

          Chemistry
          concerted reactions ,csnar mechanism,meisenheimer complex,nucleophilic aromatic substitution

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