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

ABSTRACT: 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.

SUBMITTER: Wu J

PROVIDER: S-EPMC11301629 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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

Wu Jun J Purushothaman Rajeshwaran R Kallert Felix F Homölle Simon L SL Ackermann Lutz L

ACS catalysis 20240719 15

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 o ...[more]

PMID: 39114086

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