Visible-Light-Mediated Stadler-Ziegler Arylation of Thiosugars with Anilines

Mingxiang Zhu; Juba Ghouilem; Samir Messaoudi

doi:10.1021/acsorginorgau.2c00006

Visible-Light-Mediated Stadler-Ziegler Arylation of Thiosugars with Anilines

Mingxiang Zhu, Juba Ghouilem, Samir Messaoudi

Université Paris-Sud

Research output: Contribution to journal › Article › peer-review

Abstract

Here, we report a one-pot Stadler-Ziegler reaction toward the synthesis of 1-thioglycosides in good yield from commercially available anilines and (un)protected 1-glycosyl thiols. This simple and mild approach employs the photoredox catalyst [Ru(bpy)₃](PF₆)₂ under visible light.

Original language	English
Pages (from-to)	351-358
Number of pages	8
Journal	ACS Organic and Inorganic Au
Volume	2
Issue number	4
DOIs	https://doi.org/10.1021/acsorginorgau.2c00006
Publication status	Published - 3 Aug 2022
Externally published	Yes

Keywords

C-glycosides
Stadler−Ziegler reaction
anilines
aryl diazoniums
photoredox
thioglycosides
thiosugars

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10.1021/acsorginorgau.2c00006

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title = "Visible-Light-Mediated Stadler-Ziegler Arylation of Thiosugars with Anilines",

abstract = "Here, we report a one-pot Stadler-Ziegler reaction toward the synthesis of 1-thioglycosides in good yield from commercially available anilines and (un)protected 1-glycosyl thiols. This simple and mild approach employs the photoredox catalyst [Ru(bpy)3](PF6)2 under visible light.",

keywords = "C-glycosides, Stadler−Ziegler reaction, anilines, aryl diazoniums, photoredox, thioglycosides, thiosugars",

author = "Mingxiang Zhu and Juba Ghouilem and Samir Messaoudi",

note = "Publisher Copyright: {\textcopyright} 2022 The Authors. Published by American Chemical Society.",

year = "2022",

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doi = "10.1021/acsorginorgau.2c00006",

language = "English",

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AU - Zhu, Mingxiang

AU - Ghouilem, Juba

AU - Messaoudi, Samir

PY - 2022/8/3

Y1 - 2022/8/3

N2 - Here, we report a one-pot Stadler-Ziegler reaction toward the synthesis of 1-thioglycosides in good yield from commercially available anilines and (un)protected 1-glycosyl thiols. This simple and mild approach employs the photoredox catalyst [Ru(bpy)3](PF6)2 under visible light.

AB - Here, we report a one-pot Stadler-Ziegler reaction toward the synthesis of 1-thioglycosides in good yield from commercially available anilines and (un)protected 1-glycosyl thiols. This simple and mild approach employs the photoredox catalyst [Ru(bpy)3](PF6)2 under visible light.

KW - C-glycosides

KW - Stadler−Ziegler reaction

KW - anilines

KW - aryl diazoniums

KW - photoredox

KW - thioglycosides

KW - thiosugars

U2 - 10.1021/acsorginorgau.2c00006

DO - 10.1021/acsorginorgau.2c00006

M3 - Article

AN - SCOPUS:85138219437

SN - 2694-247X

VL - 2

SP - 351

EP - 358

JO - ACS Organic and Inorganic Au

JF - ACS Organic and Inorganic Au

IS - 4

ER -

Visible-Light-Mediated Stadler-Ziegler Arylation of Thiosugars with Anilines

Abstract

Keywords

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