Catalytic and Photochemical Strategies to Stabilized Radicals Based on Anomeric Nucleophiles.

ABSTRACT: Carbohydrates, one of the three primary macromolecules of living organisms, play significant roles in various biological processes such as intercellular communication, cell recognition, and immune activity. While the majority of established methods for the installation of carbohydrates through the anomeric carbon rely on nucleophilic displacement, anomeric radicals represent an attractive alternative because of their functional group compatibility and high anomeric selectivities. Herein, we demonstrate that anomeric nucleophiles such as C1 stannanes can be converted into anomeric radicals by merging Cu(I) catalysis with blue light irradiation to achieve highly stereoselective C(sp³)-S cross-coupling reactions. Mechanistic studies and DFT calculations revealed that the C-S bond-f

SUBMITTER: Zhu F 

PROVIDER: S-EPMC9640225 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature