Transient imine as a directing group for the Pd-catalyzed anomeric C(sp3)-H arylation of 3-aminosugars

The first example of Pd(ii)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.

Automated summary

This study presents a novel method for the Pd(ii)-catalyzed arylation of 3-aminosugars using a transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine is transformed into an azide function, which is further utilized in a CuAAC reaction to generate complex substituted C3-triazolo C-glycosides with high yields.