Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides

A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis of nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple reaction system, high diastereoselectivity, and good fun...

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Veröffentlicht in:Journal of organic chemistry 2025-01
Hauptverfasser: Lv, Guanghui, Wang, Yangyang, Zhang, Penghua, Zhu, Yafei, Wang, Mi, Ma, Zhaohui, Zhang, Cuimei, Chen, Jian, Guo, Li, Wu, Yong
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Sprache:eng
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Zusammenfassung:A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis of nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents the need for high temperature, transition metal, and photocatalyst, offering an environmentally friendly and efficient protocol.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02528