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Nickel-Mediated Synthesis of Non-Anomeric C‑Acyl Glycosides through Electron Donor–Acceptor Complex Photoactivation

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journal contribution
posted on 15.03.2022, 14:33 authored by Marcos Escolano, María Jesús Cabrera-Afonso, Maria Ribagorda, Shorouk O. Badir, Gary A. Molander
The preparation of nonanomeric C-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.