Synthesis of N-Glycosyl-2-oxindoles by Pd-Catalyzed N-Arylation of 1-Amidosugars

Boris Letribot; Wafa Redjdal; Wafa Redjdal; Belkacem Benmerad; Franck Le Bideau; Mouâd Alami; Samir Messaoudi

doi:10.1021/acs.orglett.0c01262

Synthesis of N-Glycosyl-2-oxindoles by Pd-Catalyzed N-Arylation of 1-Amidosugars

Boris Letribot
, Wafa Redjdal
, Wafa Redjdal
, Belkacem Benmerad
, Franck Le Bideau
, Mouâd Alami
, Samir Messaoudi

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

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

11 Citations (Scopus)

Abstract

An efficient intramolecular Pd-catalyzed N-arylation of o-iodo-amidosugars for the synthesis of N-glycosylated oxindoles has been reported. The coupling reaction takes place in toluene and involves Pd(OAc)2/RuPhos catalytic systems in the presence of K2CO3. This versatile approach was extended successfully to the synthesis of other N-glycosylated heterocycles.

Original language	English
Pages (from-to)	4201-4206
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.0c01262
Publication status	Published - 5 Jun 2020
Externally published	Yes

Access to Document

10.1021/acs.orglett.0c01262

Cite this

@article{775c9a39c0de4960884c22e10bc4b945,

title = "Synthesis of N-Glycosyl-2-oxindoles by Pd-Catalyzed N-Arylation of 1-Amidosugars",

abstract = "An efficient intramolecular Pd-catalyzed N-arylation of o-iodo-amidosugars for the synthesis of N-glycosylated oxindoles has been reported. The coupling reaction takes place in toluene and involves Pd(OAc)2/RuPhos catalytic systems in the presence of K2CO3. This versatile approach was extended successfully to the synthesis of other N-glycosylated heterocycles.",

author = "Boris Letribot and Wafa Redjdal and Wafa Redjdal and Belkacem Benmerad and \{Le Bideau\}, Franck and Mou{\^a}d Alami and Samir Messaoudi",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = jun,

day = "5",

doi = "10.1021/acs.orglett.0c01262",

language = "English",

volume = "22",

pages = "4201--4206",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Synthesis of N-Glycosyl-2-oxindoles by Pd-Catalyzed N-Arylation of 1-Amidosugars

AU - Letribot, Boris

AU - Redjdal, Wafa

AU - Benmerad, Belkacem

AU - Le Bideau, Franck

AU - Alami, Mouâd

AU - Messaoudi, Samir

PY - 2020/6/5

Y1 - 2020/6/5

N2 - An efficient intramolecular Pd-catalyzed N-arylation of o-iodo-amidosugars for the synthesis of N-glycosylated oxindoles has been reported. The coupling reaction takes place in toluene and involves Pd(OAc)2/RuPhos catalytic systems in the presence of K2CO3. This versatile approach was extended successfully to the synthesis of other N-glycosylated heterocycles.

AB - An efficient intramolecular Pd-catalyzed N-arylation of o-iodo-amidosugars for the synthesis of N-glycosylated oxindoles has been reported. The coupling reaction takes place in toluene and involves Pd(OAc)2/RuPhos catalytic systems in the presence of K2CO3. This versatile approach was extended successfully to the synthesis of other N-glycosylated heterocycles.

U2 - 10.1021/acs.orglett.0c01262

DO - 10.1021/acs.orglett.0c01262

M3 - Article

C2 - 32401034

AN - SCOPUS:85085657349

SN - 1523-7060

VL - 22

SP - 4201

EP - 4206

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Synthesis of N-Glycosyl-2-oxindoles by Pd-Catalyzed N-Arylation of 1-Amidosugars

Abstract

Access to Document

Fingerprint

Cite this