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Copper‐Catalyzed Regioselective Direct C–H Thiolation and Thiocyanation of Uracils
Author(s) -
Noikham Medena,
Yotphan Sirilata
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900343
Subject(s) - chemistry , regioselectivity , reagent , combinatorial chemistry , bond cleavage , catalysis , thiocyanate , thio , uracil , cleavage (geology) , copper , organic chemistry , dna , biochemistry , geotechnical engineering , fracture (geology) , engineering
A novel copper‐catalyzed direct C–H thiolation and thiocyanation of uracils using disulfides and thiocyanate salts respectively as coupling partners are described. These reactions enable the C–H bond cleavage and C–S bond formation to proceed efficiently under relatively mild conditions, providing useful methods for a preparation of a series of thio‐substituted at the C5 position of uracil derivatives. These protocols exhibit several merits including simple experimental procedures, readily accessible substrates and reagents, broad scopes, high yields, and excellent regioselectivity. Preliminary mechanistic studies revealed that a radical pathway is likely to be involved.