Concerted nucleophilic aromatic substitution reactions

Simon Rohrbach, Andrew J. Smith, Jia Hao Pang, Darren L. Poole, Tell Tuttle, Shunsuke Chiba, John A. Murphy

Research output: Contribution to journalArticle

31 Citations (Scopus)
463 Downloads (Pure)

Abstract

Recent developments in experimental and computational chemistry have identified a rapidly growing class of nucleophilic aromatic substitutions that proceed by concerted (cSNAr) rather than classical, two-step, SNAr mechanisms. Whereas traditional SNAr reactions require substantial activation of the aromatic ring by electron-withdrawing substituents, such activating groups are not mandatory in the concerted pathways. At this crucial stage of growth in understanding of these reactions, our aim is to review the current state of knowledge on cSNAr reactions. [The review includes many types of substrates and nucleophiles; it specifically excludes transition metal-related processes that might involve concerted substitutions on arenes].
Original languageEnglish
Pages (from-to)16368-16388
Number of pages21
JournalAngewandte Chemie International Edition
Volume58
Issue number46
Early online date16 Apr 2019
DOIs
Publication statusPublished - 11 Nov 2019

Keywords

  • nucleophilic aromatic substitutions
  • substitution reactions
  • electron transfer

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