An efficient thioglycosylation of C(sp )-H bonds with thiosugars has been established for the first time. Using only Cu(OAc) ⋅H O as a catalyst and Ag CO as an additive in DMSO, the protocol proved to have broad scope, and a variety of complex thioglycosides have been prepared in good yields with exclusive β-selectivity.
A range of unsymmetrical biaryls bearing thiosugars could be synthesized in a one-pot multicomponent approach using one catalytic palladium system that permitted the C-S and C-C bonds to be formed sequentially. The reaction showed a high selectivity and was applied to a broad variety of substrates giving access to novel glycosylated biaryl structures in good yields.
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