Palladium(II)-Catalyzed Diastereoselective 2,3-Trans C(sp3)-H Arylation of Glycosides

Nicolas Probst; Gwendal Grelier; Slimane Dahaoui; Mouâd Alami; Vincent Gandon; Samir Messaoudi

doi:10.1021/acscatal.8b01617

Palladium(II)-Catalyzed Diastereoselective 2,3-Trans C(sp³)-H Arylation of Glycosides

Nicolas Probst
, Gwendal Grelier
, Slimane Dahaoui
, Mouâd Alami
, Vincent Gandon
, Samir Messaoudi

Université Paris-Sud
Institut de Chimie des Substances Naturelles
Nancy Université
Université Paris-Saclay
Institut de Chimie Moléculaire et des Matériaux d'Orsay

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

57 Citations (Scopus)

Abstract

We report herein the diastereoselective C(sp³)-H arylation of glycosides. A wide range of β- and α-glycosides proved able to selectively undergo Pd(II)-catalyzed coupling with diverse aryl iodides to assemble a large library of functionalized 3-arylglycosylamides. DFT calculations were performed to elucidate the unexpected trans stereoselectivity of this reaction.

Original language	English
Pages (from-to)	7781-7786
Number of pages	6
Journal	ACS Catalysis
Volume	8
Issue number	9
DOIs	https://doi.org/10.1021/acscatal.8b01617
Publication status	Published - 7 Sept 2018
Externally published	Yes

Keywords

C(sp)-H activation
C-glycosides
DFT calculations
carbohydrate
palladium catalysis

Access to Document

10.1021/acscatal.8b01617

Cite this

@article{606d1565b1b0415fa3428354d7f173fd,

title = "Palladium(II)-Catalyzed Diastereoselective 2,3-Trans C(sp3)-H Arylation of Glycosides",

abstract = "We report herein the diastereoselective C(sp3)-H arylation of glycosides. A wide range of β- and α-glycosides proved able to selectively undergo Pd(II)-catalyzed coupling with diverse aryl iodides to assemble a large library of functionalized 3-arylglycosylamides. DFT calculations were performed to elucidate the unexpected trans stereoselectivity of this reaction.",

keywords = "C(sp)-H activation, C-glycosides, DFT calculations, carbohydrate, palladium catalysis",

author = "Nicolas Probst and Gwendal Grelier and Slimane Dahaoui and Mou{\^a}d Alami and Vincent Gandon and Samir Messaoudi",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = sep,

day = "7",

doi = "10.1021/acscatal.8b01617",

language = "English",

volume = "8",

pages = "7781--7786",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Palladium(II)-Catalyzed Diastereoselective 2,3-Trans C(sp3)-H Arylation of Glycosides

AU - Probst, Nicolas

AU - Grelier, Gwendal

AU - Dahaoui, Slimane

AU - Alami, Mouâd

AU - Gandon, Vincent

AU - Messaoudi, Samir

PY - 2018/9/7

Y1 - 2018/9/7

N2 - We report herein the diastereoselective C(sp3)-H arylation of glycosides. A wide range of β- and α-glycosides proved able to selectively undergo Pd(II)-catalyzed coupling with diverse aryl iodides to assemble a large library of functionalized 3-arylglycosylamides. DFT calculations were performed to elucidate the unexpected trans stereoselectivity of this reaction.

AB - We report herein the diastereoselective C(sp3)-H arylation of glycosides. A wide range of β- and α-glycosides proved able to selectively undergo Pd(II)-catalyzed coupling with diverse aryl iodides to assemble a large library of functionalized 3-arylglycosylamides. DFT calculations were performed to elucidate the unexpected trans stereoselectivity of this reaction.

KW - C(sp)-H activation

KW - C-glycosides

KW - DFT calculations

KW - carbohydrate

KW - palladium catalysis

U2 - 10.1021/acscatal.8b01617

DO - 10.1021/acscatal.8b01617

M3 - Article

AN - SCOPUS:85049926607

SN - 2155-5435

VL - 8

SP - 7781

EP - 7786

JO - ACS Catalysis

JF - ACS Catalysis

IS - 9