Concerted nucleophilic aromatic substitution reactions

Rohrbach, Simon and Smith, Andrew J. and Pang, Jia Hao and Poole, Darren L. and Tuttle, Tell and Chiba, Shunsuke and Murphy, John A. (2019) Concerted nucleophilic aromatic substitution reactions. Angewandte Chemie International Edition, 58 (46). pp. 16368-16388. ISSN 1433-7851

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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 (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].