A convenient and straightforward synthesis of diverse 2-C-alkenyl-glycosides through a palladium-catalyzed cross-coupling reaction between 2-iodoglycals and N-tosylhydrazones has been developed. Further transformation of 2-Cbranched sugars by Diels−Alder reactions provided oxadecalins in good yields.

Palladium-catalyzed arylation/heteroarylation of aryl halide-tethered alkenes with propargylic pyridines has been established, which provides direct and efficient access to various oxindole, azaoxindole, dihydrobenzopyran, indole, and benzofuranlinked indolizines in good yields with a broad substrate scope and high functional group tolerance. This process enables the formation of one C−N and two C−C bonds in a single operation through an intramolecular carbopalladation and cycloisomerization sequence. Furthermore, an indolizinone-linked bisheterocyclic framework containing indole and benzofuran could be synthesized conveniently from tertiary propargylic alcohols involving methyl or phenyl migration.

An efficient and practical approach for the synthesis of 3-indolyl-C-∆1,2–glycosides through a palladium-catalyzed annulation/C-glycosylation sequence of o-alkynylanilines with 1-iodoglycals has been developed. This methodology has a wide scope of substrates...

No abstract

By turning on or switching off the directing effect of the C3–OH-located o-diphenylphosphanylbenzoyl (o-DPPB) group in glycals, a reagent-controlled protocol for divergent and regio- and stereoselective syntheses of C-glycosides has been established. In particular, the silence of the directing effect of o-DPPB was achieved by the introduction of a ZnCl2 additive, which is operationally simple and efficient. The flexibility of the novel protocol was exhibited not only by the easy access of both α- and β-C-glycosides but also by the versatility of the obtained formal Ferrier rearrangement products, which can be easily derivatized to various C-glycoside analogues owing to the embedded multifunctionalities.