Photocatalytic, site-selective oxidations of carbohydrates

Site-selective oxidations of carbohydrates, employing acridinium photocatalysis and quinuclidine hydrogen atom transfer catalysis, are presented. Protocols have been developed for oxidations of all-equatorial carbohydrates as well as those containing cis-1,2-diols. Site-selectivity reflects the relative rates of hydrogen atom transfer from the carbohydrate C-H bonds, and can be enhanced using a phosphate hydrogen-bonding or boronic acid catalyst.

Automated summary

Site-selective oxidations of carbohydrates have been achieved using acridinium photocatalysis and quinuclidine hydrogen atom transfer catalysis. Protocols have been developed for oxidations of all-equatorial carbohydrates and those containing cis-1,2-diols. The site-selectivity is determined by the relative rates of hydrogen atom transfer from the carbohydrate C-H bonds and can be enhanced using a phosphate hydrogen-bonding or boronic acid catalyst.