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Visible‐Light‐Mediated Selective Arylation of Cysteine in Batch and Flow
Author(s) -
Bottecchia Cecilia,
Rubens Maarten,
Gunnoo Smita B.,
Hessel Volker,
Madder Annemieke,
Noël Timothy
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201706700
Subject(s) - cysteine , chemistry , combinatorial chemistry , phosphate buffered saline , flow chemistry , eosin y , reaction conditions , biocompatible material , photocatalysis , catalysis , visible spectrum , batch reactor , organic chemistry , chromatography , materials science , medicine , optoelectronics , biomedical engineering , enzyme
A mild visible‐light‐mediated strategy for cysteine arylation is presented. The method relies on the use of eosin Y as a metal‐free photocatalyst and aryldiazonium salts as arylating agents. The reaction can be significantly accelerated in a microflow reactor, whilst allowing the in situ formation of the required diazonium salts. The batch and flow protocol described herein can be applied to obtain a broad series of arylated cysteine derivatives and arylated cysteine‐containing dipeptides. Moreover, the method was applied to the chemoselective arylation of a model peptide in biocompatible reaction conditions (room temperature, phosphate‐buffered saline (PBS) buffer) within a short reaction time.