Literature DB >> 26368348

Nucleophilic Aromatic Substitution Reactions in Water Enabled by Micellar Catalysis.

Nicholas A Isley1, Roscoe T H Linstadt1, Sean M Kelly1, Fabrice Gallou2, Bruce H Lipshutz1.   

Abstract

Given the huge dependence on dipolar, aprotic solvents such as DMF, DMSO, DMAc, and NMP in nucleophilic aromatic substitution reactions (SNAr), a simple and environmentally friendly alternative is reported. Use of a "benign-by-design" nonionic surfactant, TPGS-750-M, in water enables nitrogen, oxygen, and sulfur nucleophiles to participate in SNAr reactions. Aromatic and heteroaromatic substrates readily participate in this micellar catalysis, which takes place at or near ambient temperatures.

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Year:  2015        PMID: 26368348     DOI: 10.1021/acs.orglett.5b02240

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

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Review 2.  Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives.

Authors:  Andrew Jordan; Callum G J Hall; Lee R Thorp; Helen F Sneddon
Journal:  Chem Rev       Date:  2022-02-24       Impact factor: 72.087

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Authors:  Stephen Wallace; Emily P Balskus
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-08       Impact factor: 15.336

4.  Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution.

Authors:  Jiho Song; Hae Ju Kang; Jung Wuk Lee; Michelle A Wenas; Seung Hwarn Jeong; Taeho Lee; Kyungsoo Oh; Kyung Hoon Min
Journal:  PLoS One       Date:  2017-08-23       Impact factor: 3.240

5.  Chromatography-Free Multicomponent Synthesis of Thioureas Enabled by Aqueous Solution of Elemental Sulfur.

Authors:  András Gy Németh; Renáta Szabó; Attila Domján; György M Keserű; Péter Ábrányi-Balogh
Journal:  ChemistryOpen       Date:  2020-12-30       Impact factor: 2.630

6.  Synthesis of Benzo[4,5]thiazolo[2,3-c][1,2,4]triazole Derivatives via C-H Bond Functionalization of Disulfide Intermediates.

Authors:  Luis G Ardón-Muñoz; Jeanne L Bolliger
Journal:  Molecules       Date:  2022-02-22       Impact factor: 4.411

Review 7.  The Potential of Micellar Media in the Synthesis of DNA-Encoded Libraries.

Authors:  Réka Adamik; Balázs Buchholcz; Ferenc Darvas; Gellért Sipos; Zoltán Novák
Journal:  Chemistry       Date:  2022-02-14       Impact factor: 5.020

8.  Encapsulation of catalyst in block copolymer micelles for the polymerization of ethylene in aqueous medium.

Authors:  Camille Boucher-Jacobs; Muhammad Rabnawaz; Joshua S Katz; Ralph Even; Damien Guironnet
Journal:  Nat Commun       Date:  2018-02-26       Impact factor: 14.919

  8 in total

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