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Updated: Nov 4, 2025

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Published on: January 19, 2016
Light-Mediated Cross-Coupling of Anomeric Trifluoroborates
Eric M Miller1, Maciej A Walczak1
1Department of Chemistry, University of Colorado, Boulder, Colorado 80309, United States.
Abstract:
Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report stereoselective C-arylation and etherification reactions of anomeric trifluoroborates derived from BMIDA esters. These reactions are characterized by high anomeric selectivities for 2-deoxysugars and broad substrate scope (24 examples), including disaccharides and trifluoroborates with free hydroxyl groups. Taken together, this new class of carbohydrate reagents adds the palette of anomeric nucleophile reagents suitable for efficient installation of C-C bonds.
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