Stereoselective copper-catalyzed Chan–Lam–Evans N-arylation of glucosamines with arylboronic acids at room temperature

Alexandre Bruneau; Jean Daniel Brion; Mouad Alami; Samir Messaoudi

doi:10.1039/c3cc44780d

Stereoselective copper-catalyzed Chan–Lam–Evans N-arylation of glucosamines with arylboronic acids at room temperature

Alexandre Bruneau
, Jean Daniel Brion
, Mouad Alami
, Samir Messaoudi

Université Paris-Saclay

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

Abstract

An efficient and practical N-arylation of glycosylamines with substituted aryl boronic acids has been established. Using Cu(OAc)₂ and pyridine at room temperature under air atmosphere, the protocol proved to be general, and a variety of aryl N-glycosides have been prepared in good to excellent yields with exclusive β selectivity.

Original language	English
Pages (from-to)	8359-8361
Number of pages	3
Journal	Chemical Communications
Volume	49
Issue number	75
DOIs	https://doi.org/10.1039/c3cc44780d
Publication status	Published - 22 Aug 2013
Externally published	Yes

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title = "Stereoselective copper-catalyzed Chan–Lam–Evans N-arylation of glucosamines with arylboronic acids at room temperature",

abstract = "An efficient and practical N-arylation of glycosylamines with substituted aryl boronic acids has been established. Using Cu(OAc)2 and pyridine at room temperature under air atmosphere, the protocol proved to be general, and a variety of aryl N-glycosides have been prepared in good to excellent yields with exclusive β selectivity.",

author = "Alexandre Bruneau and Brion, \{Jean Daniel\} and Mouad Alami and Samir Messaoudi",

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T1 - Stereoselective copper-catalyzed Chan–Lam–Evans N-arylation of glucosamines with arylboronic acids at room temperature

AU - Bruneau, Alexandre

AU - Brion, Jean Daniel

AU - Alami, Mouad

AU - Messaoudi, Samir

PY - 2013/8/22

Y1 - 2013/8/22

N2 - An efficient and practical N-arylation of glycosylamines with substituted aryl boronic acids has been established. Using Cu(OAc)2 and pyridine at room temperature under air atmosphere, the protocol proved to be general, and a variety of aryl N-glycosides have been prepared in good to excellent yields with exclusive β selectivity.

AB - An efficient and practical N-arylation of glycosylamines with substituted aryl boronic acids has been established. Using Cu(OAc)2 and pyridine at room temperature under air atmosphere, the protocol proved to be general, and a variety of aryl N-glycosides have been prepared in good to excellent yields with exclusive β selectivity.

U2 - 10.1039/c3cc44780d

DO - 10.1039/c3cc44780d

M3 - Article

C2 - 23928939

AN - SCOPUS:84883241718

SN - 1359-7345

VL - 49

SP - 8359

EP - 8361

JO - Chemical Communications

JF - Chemical Communications

IS - 75

ER -

Stereoselective copper-catalyzed Chan–Lam–Evans N-arylation of glucosamines with arylboronic acids at room temperature

Abstract

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