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

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

^*Corresponding author for this work

Research output: Contribution to journal › Review article › peer-review

198 Citations (Scopus)

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.

Original language	English
Pages (from-to)	16368-16388
Number of pages	21
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	46
DOIs	https://doi.org/10.1002/anie.201902216
Publication status	Published - Nov 11 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

concerted reactions
cSAr mechanism
Meisenheimer complex
nucleophilic aromatic substitution

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10.1002/anie.201902216

Cite this

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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.",

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AU - Rohrbach, Simon

AU - Smith, Andrew J.

AU - Pang, Jia Hao

AU - Poole, Darren L.

AU - Tuttle, Tell

AU - Chiba, Shunsuke

AU - Murphy, John A.

PY - 2019/11/11

Y1 - 2019/11/11

N2 - 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.

AB - 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.

KW - concerted reactions

KW - cSAr mechanism

KW - Meisenheimer complex

KW - nucleophilic aromatic substitution

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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Concerted Nucleophilic Aromatic Substitution Reactions

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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