Aromatic Substitution in Water by Using a Polymeric Amphiphilic Additive

Yasuhiro Uozumi; Ryoko Niimi

doi:10.1055/s-0040-1720820

Synfacts, Table of Contents

Synfacts 2021; 17(09): 1023
DOI: 10.1055/s-0040-1720820

Polymer-Supported Synthesis

Aromatic Substitution in Water by Using a Polymeric Amphiphilic Additive

Authors

Yasuhiro Uozumi
Ryoko Niimi

Abstract

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Borlinghaus N, Ansari TN, Braje LH, Ogulu D, Handa S, Wittmann V, Braje WM. * AbbVieDeutschland GmbH & Co. KG, Ludwingshafen, Germany
Nucleophilic Aromatic Substitution Reactions under Aqueous, Mild Conditions Using Polymeric Additive HPMC.

Green Chem. 2021;
23: 3955-3962
DOI: 10.1039/d1gc00128k

Key words

aqueous media - aromatic substitution - aryl halides - polysaccharides - aromatic amination - S_NAr reaction

Significance

S_NAr amination reactions of various aryl fluorides or chlorides with amine nucleophiles was achieved in water in the presence of amphiphilic hydroxypropyl methylcellulose (HPMC). The aqueous HPMC phase could be reused in consecutive runs.

Comment

A lipophilic reaction pocket formed by folding of HPMC in water promotes the organic reaction. S_NAr reactions with thiols or a benzylic alcohol were also examined.

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