Nickel-Mediated Synthesis of Non-Anomeric <i>C</i>-Acyl Glycosides through Electron Donor–Acceptor Complex Photoactivation
Marcos Escolano, María Jesús Cabrera‐Afonso, M. Ribagorda, Shorouk O. Badir, Gary A. Molander
Abstract
-acyl-saccharides has been developed from two different carboxylic acid feedstocks. This transformation is driven by the synergistic interaction of an electron donor-acceptor complex and Ni catalysis. Primary-, secondary-, and tertiary redox-active esters are incorporated as coupling partners onto preactivated pyranosyl- and furanosyl acids, preserving their stereochemical integrity. The reaction occurs under mild conditions, without stoichiometric metal reductants or exogenous catalysts, using commercially available Hantzsch ester as the organic photoreductant.
Topics & Concepts
ChemistryAnomerCatalysisElectron acceptorAcceptorRedoxNickelCarboxylic acidStoichiometryElectron donorCombinatorial chemistryLigand (biochemistry)Organic chemistryReceptorBiochemistryCondensed matter physicsPhysicsCarbohydrate Chemistry and SynthesisRadical Photochemical ReactionsSynthesis of Indole Derivatives