Pd-Catalyzed Ortho-Directed C-H Glycosylation of Arenes Using N-linked Bidentate Auxiliaries

Main observation and conclusion A set of Pd-catalyzed ortho-directed C-H glycosylation reactions with glycosyl chloride donors using various N-linked bidentate auxiliaries has been developed for synthesis of C-aryl glycosides. A broad range of pyranose and furanose moieties can be installed on the ortho position of arylamine, carbazole, indole and benzylamine type substrates in high yield and with high regio- and diastereoselectivity. These auxiliaries can be readily installed and removed under relatively mild conditions.

Automated summary

A novel Pd-catalyzed ortho-directed C-H glycosylation reaction using N-linked bidentate auxiliaries has been developed for efficient synthesis of C-aryl glycosides with high yield and selectivity. This method allows for installation of a wide range of pyranose and furanose moieties on various substrates and facile installation and removal of the auxiliaries under mild conditions.