Diastereoselective Pd-Catalyzed Anomeric C(sp3)-H Activation: Synthesis of α-(Hetero)aryl C-Glycosides

Juba Ghouilem; Christine Tran; Nicolas Grimblat; Pascal Retailleau; Mouad Alami; Vincent Gandon; Samir Messaoudi

doi:10.1021/acscatal.0c05052

Diastereoselective Pd-Catalyzed Anomeric C(sp³)-H Activation: Synthesis of α-(Hetero)aryl C-Glycosides

Juba Ghouilem
, Christine Tran
, Nicolas Grimblat
, Pascal Retailleau
, Mouad Alami
, Vincent Gandon
, Samir Messaoudi

Université Paris-Saclay
CNRS
Universidad Nacional de Rosario

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

67 Citations (Scopus)

Abstract

Anomeric C-H bond activation is an unsolved long-standing synthetic challenge. Herein, we report a diastereoselective Pd-catalyzed anomeric C(sp3)-H activation methodology that allows the synthesis of elusive C-(hetero)aryl glycosides with an exclusive α-selectivity.

Original language	English
Pages (from-to)	1818-1826
Number of pages	9
Journal	ACS Catalysis
Volume	11
Issue number	3
DOIs	https://doi.org/10.1021/acscatal.0c05052
Publication status	Published - 5 Feb 2021
Externally published	Yes

Keywords

C(sp)-H functionalization
C-glycosides
DFT calculations
carbohydrates
glycosylation

Access to Document

10.1021/acscatal.0c05052

Cite this

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title = "Diastereoselective Pd-Catalyzed Anomeric C(sp3)-H Activation: Synthesis of α-(Hetero)aryl C-Glycosides",

abstract = "Anomeric C-H bond activation is an unsolved long-standing synthetic challenge. Herein, we report a diastereoselective Pd-catalyzed anomeric C(sp3)-H activation methodology that allows the synthesis of elusive C-(hetero)aryl glycosides with an exclusive α-selectivity.",

keywords = "C(sp)-H functionalization, C-glycosides, DFT calculations, carbohydrates, glycosylation",

author = "Juba Ghouilem and Christine Tran and Nicolas Grimblat and Pascal Retailleau and Mouad Alami and Vincent Gandon and Samir Messaoudi",

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AU - Ghouilem, Juba

AU - Tran, Christine

AU - Grimblat, Nicolas

AU - Retailleau, Pascal

AU - Alami, Mouad

AU - Gandon, Vincent

AU - Messaoudi, Samir

N1 - Publisher Copyright: ©

PY - 2021/2/5

Y1 - 2021/2/5

N2 - Anomeric C-H bond activation is an unsolved long-standing synthetic challenge. Herein, we report a diastereoselective Pd-catalyzed anomeric C(sp3)-H activation methodology that allows the synthesis of elusive C-(hetero)aryl glycosides with an exclusive α-selectivity.

AB - Anomeric C-H bond activation is an unsolved long-standing synthetic challenge. Herein, we report a diastereoselective Pd-catalyzed anomeric C(sp3)-H activation methodology that allows the synthesis of elusive C-(hetero)aryl glycosides with an exclusive α-selectivity.

KW - C(sp)-H functionalization

KW - C-glycosides

KW - DFT calculations

KW - carbohydrates

KW - glycosylation

U2 - 10.1021/acscatal.0c05052

DO - 10.1021/acscatal.0c05052

M3 - Article

AN - SCOPUS:85100819111

SN - 2155-5435

VL - 11

SP - 1818

EP - 1826

JO - ACS Catalysis

JF - ACS Catalysis

IS - 3