Transient imine as a directing group for the Pd-catalyzed anomeric C(sp3)–H arylation of 3-aminosugars

Juba Ghouilem; Sokna Bazzi; Nicolas Grimblat; Pascal Retailleau; Vincent Gandon; Samir Messaoudi

doi:10.1039/D3CC00046J

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Transient imine as a directing group for the Pd-catalyzed anomeric C(sp³)–H arylation of 3-aminosugars†

Juba Ghouilem,^a Sokna Bazzi,^a Nicolas Grimblat,

^b Pascal Retailleau,^c Vincent Gandon

^bd and Samir Messaoudi

*^a

Author affiliations

* Corresponding authors

^a Universite Paris-Saclay, CNRS, BioCIS, Châtenay-Malabry, France
E-mail: samir.messaoudi@universite-paris-saclay.fr
Tel: +(33) 0146835887

^b Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, route de Saclay, Palaiseau 91120, France

^c Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Universite Paris-Saclay, avenue de la terrasse, Gif-sur-Yvette 91198, France

^d Université Paris-Saclay, CNRS, ICMMO, Orsay cedex, France

Abstract

The first example of Pd(II)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.

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Article information

DOI: https://doi.org/10.1039/D3CC00046J
Article type: Communication
Submitted: 03 Jan 2023
Accepted: 30 Jan 2023
First published: 31 Jan 2023
This article is Open Access

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Chem. Commun., 2023,59, 2497-2500

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Transient imine as a directing group for the Pd-catalyzed anomeric C(sp³)–H arylation of 3-aminosugars

J. Ghouilem, S. Bazzi, N. Grimblat, P. Retailleau, V. Gandon and S. Messaoudi, Chem. Commun., 2023, 59, 2497 DOI: 10.1039/D3CC00046J

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