Concerted Nucleophilic Aromatic Substitution Reactions

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

doi:10.1002/anie.201902216

Concerted Nucleophilic Aromatic Substitution Reactions

Angew Chem Int Ed Engl. 2019 Nov 11;58(46):16368-16388. doi: 10.1002/anie.201902216. Epub 2019 Sep 13.

Authors

Simon Rohrbach¹, Andrew J Smith¹, Jia Hao Pang², Darren L Poole³, Tell Tuttle¹, Shunsuke Chiba², John A Murphy¹

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.

Abstract

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

Keywords: Meisenheimer complex; cSNAr mechanism; concerted reactions; nucleophilic aromatic substitution.

Publication types

Review

Abstract

Publication types

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