M. Lautens, E. Larin
May 20, 2019
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Synfacts
Abstract
Significance: Owing to their biological significance, there is strong interest in developing methods that can be used to functionalize carbohydrate C–H sites selectively and efficiently. The authors report a stereoand site-selective C–H alkylation of carbohydrate derivatives. This is achieved through a combination of diarylborinic acid and photoredox catalysis. Comment: With support from computational studies and experimental evidence, the authors propose that the formation of a tetracoordinate diarylborinic ester helps to facilitate a site-selective hydrogen-atom transfer (HAT) from the C2 position onto the HAT mediator, quinuclidine. R2 H OH