Stereoselective β‐C‐aryl Glycosylation Through Ni‐Catalyzed Reductive Cross‐Coupling
Abstract
In comparison to well-documented methods for accessing α-C-aryl glycosides,the stereoselective synthesis ofβ-anomers remains challenging, as less reliable routes to β-functionalisation are established. Metal-catalyzed cross-coupling is known as one of the most straightforward methods to afford stereoselectively β-C-aryl glycosides, this strategy often requires the use of elaborated glycosyl donors or sensitive aryl metals along with the use of strict anhydrous and oxygen-free conditions. Herein, we report a robust and stereoselective synthesis of β-C-aryl glycosides by Ni-catalyzed reductive cross-coupling using readily available and bench-stable materials. This reaction couples glycosyl halides and aryl halides in the presence of an air-stable Ni⁰ pre-catalyst and a mild reductant. The reaction exhibits excellent β-stereoselectivity with a broad range of carbohydrates and aryl moieties. Mechanistic studies, supported by density functional theory calculations, were performed to provide a rationale for the observed β-stereoselectivity.
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BibTeX
@article{crespin2026stereoselective,
title = {{Stereoselective β‐C‐aryl Glycosylation Through Ni‐Catalyzed Reductive Cross‐Coupling}},
author = {Victor Crespin and Abir Jertila and Eric Daiann Sosa Carrizo and Elsa van Elslande and Tanguy Saget and Stéphanie Norsikian and Marie Sircoglou and Sébastien Vidal},
journal = {ChemistryEurope},
year = {2026},
month = sep,
doi = {10.1002/ceur.202500477},
url = {https://hal.science/hal-05740111v1},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Stereoselective β‐C‐aryl Glycosylation Through Ni‐Catalyzed Reductive Cross‐Coupling
AU - Victor Crespin
AU - Abir Jertila
AU - Eric Daiann Sosa Carrizo
AU - Elsa van Elslande
AU - Tanguy Saget
AU - Stéphanie Norsikian
AU - Marie Sircoglou
AU - Sébastien Vidal
PY - 2026
DA - 2026/09/06
JO - ChemistryEurope
DO - 10.1002/ceur.202500477
UR - https://hal.science/hal-05740111v1
AB - In comparison to well-documented methods for accessing α-C-aryl glycosides,the stereoselective synthesis ofβ-anomers remains challenging, as less reliable routes to β-functionalisation are established. Metal-catalyzed cross-coupling is known as one of the most straightforward methods to afford stereoselectively β-C-aryl glycosides, this strategy often requires the use of elaborated glycosyl donors or sensitive aryl metals along with the use of strict anhydrous and oxygen-free conditions. Herein, we report a robust and stereoselective synthesis of β-C-aryl glycosides by Ni-catalyzed reductive cross-coupling using readily available and bench-stable materials. This reaction couples glycosyl halides and aryl halides in the presence of an air-stable Ni⁰ pre-catalyst and a mild reductant. The reaction exhibits excellent β-stereoselectivity with a broad range of carbohydrates and aryl moieties. Mechanistic studies, supported by density functional theory calculations, were performed to provide a rationale for the observed β-stereoselectivity.
SN - 2751-4765
ER -