Directed Palladium-Catalyzed pseudo-Anomeric C-H Functionalization of Glycal-Type Substrates: Access to Unsymmetrical gem-Diarylmethyl C-Glycosides

Pd(II)-Catalyzed, bidentate directing group (BDG)-assisted C(sp(2))-H functionalization of C2-amido glycals onto the anomeric position is described as a contemporary method for the construction of various unsymmetrical gem-diarylmethyl C-glycosides. Thanks to a bidentate amidoquinoline-type directing group, the insertion of diverse para-quinone methides (p-QMs) onto the pseudo-anomeric position of glycal substrates were executed in moderate to good yields. Further functionalization of the final product can be successfully demonstrated by known palladium-catalyzed cross- coupling reactions.

Automated summary

A Pd(II)-catalyzed, bidentate directing group (BDG)-assisted C(sp(2))-H functionalization of C2-amido glycals onto the anomeric position is reported as a contemporary approach for the synthesis of various unsymmetrical gem-diarylmethyl C-glycosides. The use of a bidentate amidoquinoline-type directing group enables the insertion of different para-quinone methides (p-QMs) onto the pseudo-anomeric position of glycal substrates, yielding moderate to good yields. The final product can be further functionalized through known palladium-catalyzed cross-coupling reactions.