Transient imine as a directing group for the Pd-catalyzed anomeric C(sp<sup>3</sup>)–H arylation of 3-aminosugars-Reference-Cited by-同舟云学术

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

Published:2023 Issue:17 Volume:59 Page:2497-2500
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Ghouilem Juba¹,Bazzi Sokna¹,Grimblat Nicolas²^ORCID,Retailleau Pascal³,Gandon Vincent²⁴^ORCID,Messaoudi Samir¹^ORCID

Affiliation:

1. Universite Paris-Saclay, CNRS, BioCIS, 92290, Châtenay-Malabry, France

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

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

4. Université Paris-Saclay, CNRS, ICMMO, 91405, Orsay cedex, France

Abstract

The first example of Pd(ii)-catalyzed anomeric C(sp3)–H arylation of 3-aminosugars by using a transient directing group approach is reported. The free amine was then exploited in a CuAAC reaction to access to a variety of C3-triazoloC-glycosides in good yields.

Funder

Agence Nationale de la Recherche

Centre National de la Recherche Scientifique

Université Paris-Saclay

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2023/CC/D3CC00046J

Reference36 articles.

1. C-Nucleosides: Synthetic Strategies and Biological Applications

2. C-Nucleosides To Be Revisited

3. Recent Advances in the Chemical Synthesis of C-Glycosides

4. Total Synthesis of Aryl C-Glycoside Natural Products: Strategies and Tactics

5. C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential