Ni/Photoredox-Dual-Catalyzed Functionalization of 1-Thiosugars | Zendy

Mingxiang Zhu | Zendy; Guillaume Dagousset | Zendy; Mouâd Alami | Zendy; Emmanuel Magnier | Zendy; Samir Messaoudi | Zendy

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Ni/Photoredox-Dual-Catalyzed Functionalization of 1-Thiosugars

Author(s) -

Mingxiang Zhu,

Guillaume Dagousset,

Mouâd Alami,

Emmanuel Magnier,

Samir Messaoudi

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b01730

Subject(s) - chemistry , surface modification , photoredox catalysis , aryl , combinatorial chemistry , catalysis , anomer , halide , glycosyl , organic chemistry , alkyl , photocatalysis

A general protocol for functionalization of glycosyl thiols has been reported. This protocol is based on a single-electron Ni/photoredox dual-catalyzed cross coupling between 1-thiosugars and a broad range of aryl bromides and iodides as well as alkenyl and alkynyl halides. This base-free method gives access to a series of functionalized thioglycosides in moderate to excellent yields with a perfect control of the anomeric configuration. Moreover, it has been shown that this methodology may be transposed successfully to the continuous-flow photoredox chemistry.

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