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

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

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.

Original language	English
Pages (from-to)	15006-15010
Number of pages	5
Journal	Chemistry - A European Journal
Volume	22
Issue number	42
DOIs	https://doi.org/10.1002/chem.201602909
Publication status	Published - 10 Oct 2016
Externally published	Yes

Keywords

C−H bond activation
copper
homogeneous catalysis
thioglycosides
thioglycosylation reaction

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10.1002/chem.201602909

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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",

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doi = "10.1002/chem.201602909",

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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

UR - https://www.scopus.com/pages/publications/84989950314

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

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Keywords

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