Light-Mediated Ring-Opening Functionalization of Epoxides via a Fluorinated Thiolate Mediator

Light-Mediated Ring-Opening Functionalization of Epoxides via a Fluorinated Thiolate Mediator Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2025, Volume: 27, Number: 38, Pages: 10831–10835 Pages count : DOI: 10.1021/acs.orglett.5c03458

Authors

Savchenko Artem G. ^1,2 , Zubkov Mikhail O. ² , Levin Vitalij V. ² , Dilman Alexander D. ²

Affiliations

1	Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prosp. 47, 119991 Moscow, Russian Federation

A metal-free approach to the regioselective radical ring-opening of epoxides is described. The method involves nucleophilic opening of the epoxide with a redox-active perfluorinated thiol and subsequent single-electron reduction under blue light irradiation in the presence of a stoichiometric reductant or a photocatalyst. The approach is complementary to the titanium-catalyzed processes, allows radical addition to both electron-deficient and -rich alkenes, and is also applicable to the functionalization of aziridines and bicyclobutanes.

Savchenko A.G. , Zubkov M.O. , Levin V.V. , Dilman A.D.
Light-Mediated Ring-Opening Functionalization of Epoxides via a Fluorinated Thiolate Mediator
Organic Letters. 2025. V.27. N38. P.10831–10835. DOI: 10.1021/acs.orglett.5c03458 WOS OpenAlex

Web of science:	WOS:001571610200001
OpenAlex:	W4414167176

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