Flavin-Mediated Photocatalysis Provides a General Platform for Sulfide C–H Functionalization

Functionalized sulfides are important in many areas of science, ranging from chemical biology through drug discovery to organic materials chemistry. Sulfides bearing pendant reactive groups in the α-position are particularly useful; however, methods for the selective valorization of simple sulfides...

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Bibliographic Details
Published in:ACS catalysis 2024-02, Vol.14 (4), p.2395-2401
Main Authors: Anderton, Alex S., Knowles, Oliver J., Rossi-Ashton, James A., Procter, David J.
Format: Article
Language:English
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Summary:Functionalized sulfides are important in many areas of science, ranging from chemical biology through drug discovery to organic materials chemistry. Sulfides bearing pendant reactive groups in the α-position are particularly useful; however, methods for the selective valorization of simple sulfides or the late-stage functionalization of complex sulfides by the convenient addition of valuable functionality are underexplored. Here we exemplify a general reaction platform for sulfide functionalization by showcasing three modes of α-sulfur C–H functionalization; cyanation, alkenylation, and alkynylation. Using inexpensive and commercially available riboflavin tetraacetate and visible light, decoration of both feedstock and complex sulfides proceeds in a good yield and with high selectivity. Methionine-containing peptides can also be selectively functionalized and a tolerance screen using amino-acid dopants suggests that the platform is compatible with most amino-acid side chains and thus is a potential tool for bioconjugation.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.3c05785