Non-innocent behaviour of aromatic isocyanides under visible light: a pathway to thioformimidates and dehydroalanine

Chemical Science 2026 Open access

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Authors: Minghui Wu, Jay Hanssens, Camilla Russo, Rajat Walia, Mariateresa Giustiniano, Ludovic Troian-Gautier, Jordy M. Saya, Romano V. A. Orrù, Prabhat Ranjan
DOI: 10.1039/d5sc07984e
Cited by: 1
References: 27

Abstract

Despite the significant potential of isocyanides to engage in reactions with thiyl radicals to produce nitrogen-containing organic molecules, their widespread use has been limited by the need for high-energy UV light activation. Herein, we disclose the synthesis of thioformimidates under mild reaction conditions employing visible light without additives. This study demonstrates the ability of aromatic isocyanides to generate thiyl radicals under visible light, functioning as radical intitators. Furthermore, the developed methodology reveals its utility in the selective activation of the thiol group in cysteine, which is subsequently converted to dehydroalanine, opening the door to late-stage peptide modification.

Fields of Study & Subjects

Radical Photochemical Reactions Sulfur-Based Synthesis Techniques Microwave-Assisted Synthesis and Applications

Publication details

Journal / source
Chemical Science
Publisher
Royal Society of Chemistry (RSC)
Volume
17
Issue
11
Pages
5387–5393
Publication date
1 January 2026
Language
EN