Visible-light-mediated selective arylation of cysteine in batch and flow
ArticleBottecchia, C., Rubens, M., Gunnoo, S.B., Hessel, V. & Madder, A. (2017). Visible-light-mediated selective arylation of cysteine in batch and flow. Angewandte Chemie - International Edition, 56(41), 12702–12707-12702–12707. In Scopus Cited 9 times.
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.