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Synfacts 2021; 17(09): 1023
DOI: 10.1055/s-0040-1720820
DOI: 10.1055/s-0040-1720820
Polymer-Supported Synthesis
Aromatic Substitution in Water by Using a Polymeric Amphiphilic Additive
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.
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 - SNAr reaction
Significance
SNAr 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.
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Comment
A lipophilic reaction pocket formed by folding of HPMC in water promotes the organic reaction. SNAr reactions with thiols or a benzylic alcohol were also examined.
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Publication History
Article published online:
18 August 2021
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