Electrochemical Glycosylation via Halogen-Atom-Transfer for C‑Glycoside Assembly

Glycosyl donor activation emerged as an enabling technology for anomeric functionalization, but aimed primarily at O-glycosylation. In contrast, we herein disclose mechanistically distinct electrochemical glycosyl bromide donor activations via halogen-atom transfer and anomeric C-glycosylation. The...

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Bibliographic Details
Published in:ACS catalysis 2024-08, Vol.14 (15), p.11532-11544
Main Authors: Wu, Jun, Purushothaman, Rajeshwaran, Kallert, Felix, Homölle, Simon L., Ackermann, Lutz
Format: Article
Language:English
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Summary:Glycosyl donor activation emerged as an enabling technology for anomeric functionalization, but aimed primarily at O-glycosylation. In contrast, we herein disclose mechanistically distinct electrochemical glycosyl bromide donor activations via halogen-atom transfer and anomeric C-glycosylation. The anomeric radical addition to alkenes led to C-alkyl glycoside synthesis under precious metal-free reaction conditions from readily available glycosyl bromides. The robustness of our e-XAT strategy was further mirrored by C-aryl and C-acyl glycosides assembly through nickela-electrocatalysis. Our approach provides an orthogonal strategy for glycosyl donor activation with expedient scope, hence representing a general method for direct C-glycosides assembly.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.4c02322