Literature DB >> 30990931

Concerted Nucleophilic Aromatic Substitution Reactions.

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

Abstract

Recent developments in expepan> class="Chemical">rimental and computational chemistry have identified a rapidly growing class of nucleophilic aromatic substitutions that proceed by concerted (cSN Ar) rather than classical, two-step, SN Ar mechanisms. Whereas traditional SN Ar reactions require substantial activation of the aromatic ring by electron-withdrawing substituents, such activating groups are not mandatory in the concerted pathways.
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Entities:  

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

Year:  2019        PMID: 30990931      PMCID: PMC6899550          DOI: 10.1002/anie.201902216

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  72 in total

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6.  Synthetic utilization of polynitroaromatic compounds. 6. Remarkable regioselectivity in nucleophilic displacement of aromatic nitro groups with amines.

Authors:  Konstantine A Kislyi; Alexander V Samet; Yuri A Strelenko; Victor V Semenov
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7.  How Does Nucleophilic Aromatic Substitution Really Proceed in Nitroarenes? Computational Prediction and Experimental Verification.

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8.  Expanding the palette of phenanthridinium cations.

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9.  Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings.

Authors:  Gregory J P Perry; Jacob M Quibell; Adyasha Panigrahi; Igor Larrosa
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10.  Utilizing the σ-complex stability for quantifying reactivity in nucleophilic substitution of aromatic fluorides.

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  18 in total

Review 1.  Concerted Nucleophilic Aromatic Substitution Reactions.

Authors:  Simon Rohrbach; Andrew J Smith; Jia Hao Pang; Darren L Poole; Tell Tuttle; Shunsuke Chiba; John A Murphy
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-13       Impact factor: 15.336

2.  C(sp3)-Arylation by Conformationally Accelerated Intramolecular Nucleophilic Aromatic Substitution (SNAr).

Authors:  Steven M Wales; Rakesh K Saunthwal; Jonathan Clayden
Journal:  Acc Chem Res       Date:  2022-05-27       Impact factor: 24.466

Review 3.  Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.

Authors:  Anthony R Allen; Efrey A Noten; Corey R J Stephenson
Journal:  Chem Rev       Date:  2021-10-21       Impact factor: 72.087

4.  Selective Halogenation of Pyridines Using Designed Phosphine Reagents.

Authors:  Jeffrey N Levy; Juan V Alegre-Requena; Renrong Liu; Robert S Paton; Andrew McNally
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5.  Nucleophilic Aromatic Substitution of Unactivated Fluoroarenes Enabled by Organic Photoredox Catalysis.

Authors:  Vincent A Pistritto; Megan E Schutzbach-Horton; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2020-09-28       Impact factor: 15.419

6.  Arene C-H Activation at Aluminium(I): meta Selectivity Driven by the Electronics of SN Ar Chemistry.

Authors:  Jamie Hicks; Petra Vasko; Andreas Heilmann; Jose M Goicoechea; Simon Aldridge
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7.  Hydantoin-bridged medium ring scaffolds by migratory insertion of urea-tethered nitrile anions into aromatic C-N bonds.

Authors:  Makenzie J Millward; Emily Ellis; John W Ward; Jonathan Clayden
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8.  Et3SiH + KO t Bu provide multiple reactive intermediates that compete in the reactions and rearrangements of benzylnitriles and indolenines.

Authors:  Andrew J Smith; Daniela Dimitrova; Jude N Arokianathar; Kenneth F Clark; Darren L Poole; Stuart G Leach; John A Murphy
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9.  Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines.

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10.  Computational Study on the Boundary Between the Concerted and Stepwise Mechanism of Bimolecular SNAr Reactions.

Authors:  Simon Rohrbach; John A Murphy; Tell Tuttle
Journal:  J Am Chem Soc       Date:  2020-08-20       Impact factor: 15.419

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