Stereoretentive Copper-Catalyzed Directed Thioglycosylation of C(sp2)−H Bonds of Benzamides

Amélie Chabrier; Alexandre Bruneau; Sara Benmahdjoub; Belkacem Benmerad; Sabrina Belaid; Jean Daniel Brion; Mouâd Alami; Samir Messaoudi

doi:10.1002/chem.201602909

Stereoretentive Copper-Catalyzed Directed Thioglycosylation of C(sp²)−H Bonds of Benzamides

Amélie Chabrier
, Alexandre Bruneau
, Sara Benmahdjoub
, Belkacem Benmerad
, Sabrina Belaid
, Jean Daniel Brion
, Mouâd Alami
, Samir Messaoudi

Université Paris-Sud
Laboratoire de Physico-Chimie des Matériaux et Catalyse
Université de Bejaia

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

59 Citations (Scopus)

Résumé

An efficient thioglycosylation of C(sp²)−H bonds with thiosugars has been established for the first time. Using only Cu(OAc)₂⋅H₂O as a catalyst and Ag₂CO₃as an additive in DMSO, the protocol proved to have broad scope, and a variety of complex thioglycosides have been prepared in good yields with exclusive β-selectivity.

langue originale	Anglais
Pages (de - à)	15006-15010
Nombre de pages	5
journal	Chemistry - A European Journal
Volume	22
Numéro de publication	42
Les DOIs	https://doi.org/10.1002/chem.201602909
état	Publié - 10 oct. 2016
Modification externe	Oui

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10.1002/chem.201602909

Contient cette citation

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title = "Stereoretentive Copper-Catalyzed Directed Thioglycosylation of C(sp2)−H Bonds of Benzamides",

abstract = "An efficient thioglycosylation of C(sp2)−H bonds with thiosugars has been established for the first time. Using only Cu(OAc)2⋅H2O as a catalyst and Ag2CO3as an additive in DMSO, the protocol proved to have broad scope, and a variety of complex thioglycosides have been prepared in good yields with exclusive β-selectivity.",

keywords = "C−H bond activation, copper, homogeneous catalysis, thioglycosides, thioglycosylation reaction",

author = "Am{\'e}lie Chabrier and Alexandre Bruneau and Sara Benmahdjoub and Belkacem Benmerad and Sabrina Belaid and Brion, \{Jean Daniel\} and Mou{\^a}d Alami and Samir Messaoudi",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2016",

month = oct,

day = "10",

doi = "10.1002/chem.201602909",

language = "English",

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TY - JOUR

T1 - Stereoretentive Copper-Catalyzed Directed Thioglycosylation of C(sp2)−H Bonds of Benzamides

AU - Chabrier, Amélie

AU - Bruneau, Alexandre

AU - Benmahdjoub, Sara

AU - Benmerad, Belkacem

AU - Belaid, Sabrina

AU - Brion, Jean Daniel

AU - Alami, Mouâd

AU - Messaoudi, Samir

PY - 2016/10/10

Y1 - 2016/10/10

N2 - An efficient thioglycosylation of C(sp2)−H bonds with thiosugars has been established for the first time. Using only Cu(OAc)2⋅H2O as a catalyst and Ag2CO3as an additive in DMSO, the protocol proved to have broad scope, and a variety of complex thioglycosides have been prepared in good yields with exclusive β-selectivity.

AB - An efficient thioglycosylation of C(sp2)−H bonds with thiosugars has been established for the first time. Using only Cu(OAc)2⋅H2O as a catalyst and Ag2CO3as an additive in DMSO, the protocol proved to have broad scope, and a variety of complex thioglycosides have been prepared in good yields with exclusive β-selectivity.

KW - C−H bond activation

KW - copper

KW - homogeneous catalysis

KW - thioglycosides

KW - thioglycosylation reaction

U2 - 10.1002/chem.201602909

DO - 10.1002/chem.201602909

M3 - Article

AN - SCOPUS:84989950314

SN - 0947-6539

VL - 22

SP - 15006

EP - 15010

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 42

ER -

Stereoretentive Copper-Catalyzed Directed Thioglycosylation of C(sp2)−H Bonds of Benzamides

Résumé

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Contient cette citation

Stereoretentive Copper-Catalyzed Directed Thioglycosylation of C(sp²)−H Bonds of Benzamides