Directed Dehydrogenative Copper-Catalyzed C−H Thiolation in Pseudo-Anomeric Position of Glycals using Thiol and Thiosugar Partners

Linlin Li; Lynda Mahri; Morgane de Robichon; Maha Fatthalla; Angélique Ferry; Samir Messaoudi

doi:10.1002/adsc.202200557

Directed Dehydrogenative Copper-Catalyzed C−H Thiolation in Pseudo-Anomeric Position of Glycals using Thiol and Thiosugar Partners

Linlin Li
, Lynda Mahri
, Morgane de Robichon
, Maha Fatthalla
, Angélique Ferry
, Samir Messaoudi

Université Paris-Saclay
CY Cergy Paris Université
Faculty of Science

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

The synthesis of 1-thiotrehaloses and thioglycals by a directed copper-catalyzed dehydrogenative C−H thiolation of the pseudo-anomeric bond of glycals is described. The use of aminoquinoline-containing glycals as well as thiosugars or thiols as coupling partners led to the synthesis of a library of thioglycosides in moderate to good yields. (Figure presented.).

langue originale	Anglais
Pages (de - à)	3273-3282
Nombre de pages	10
journal	Advanced Synthesis and Catalysis
Volume	364
Numéro de publication	18
Les DOIs	https://doi.org/10.1002/adsc.202200557
état	Publié - 20 sept. 2022
Modification externe	Oui

Accès au document

10.1002/adsc.202200557

Contient cette citation

@article{ba5a646365d54970aeba153b41e4aa51,

title = "Directed Dehydrogenative Copper-Catalyzed C−H Thiolation in Pseudo-Anomeric Position of Glycals using Thiol and Thiosugar Partners",

abstract = "The synthesis of 1-thiotrehaloses and thioglycals by a directed copper-catalyzed dehydrogenative C−H thiolation of the pseudo-anomeric bond of glycals is described. The use of aminoquinoline-containing glycals as well as thiosugars or thiols as coupling partners led to the synthesis of a library of thioglycosides in moderate to good yields. (Figure presented.).",

keywords = "C−H activation, copper catalysis, directing group, glycals, thiosugars",

author = "Linlin Li and Lynda Mahri and \{de Robichon\}, Morgane and Maha Fatthalla and Ang{\'e}lique Ferry and Samir Messaoudi",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = sep,

day = "20",

doi = "10.1002/adsc.202200557",

language = "English",

volume = "364",

pages = "3273--3282",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

number = "18",

}

TY - JOUR

T1 - Directed Dehydrogenative Copper-Catalyzed C−H Thiolation in Pseudo-Anomeric Position of Glycals using Thiol and Thiosugar Partners

AU - Li, Linlin

AU - Mahri, Lynda

AU - de Robichon, Morgane

AU - Fatthalla, Maha

AU - Ferry, Angélique

AU - Messaoudi, Samir

PY - 2022/9/20

Y1 - 2022/9/20

N2 - The synthesis of 1-thiotrehaloses and thioglycals by a directed copper-catalyzed dehydrogenative C−H thiolation of the pseudo-anomeric bond of glycals is described. The use of aminoquinoline-containing glycals as well as thiosugars or thiols as coupling partners led to the synthesis of a library of thioglycosides in moderate to good yields. (Figure presented.).

AB - The synthesis of 1-thiotrehaloses and thioglycals by a directed copper-catalyzed dehydrogenative C−H thiolation of the pseudo-anomeric bond of glycals is described. The use of aminoquinoline-containing glycals as well as thiosugars or thiols as coupling partners led to the synthesis of a library of thioglycosides in moderate to good yields. (Figure presented.).

KW - C−H activation

KW - copper catalysis

KW - directing group

KW - glycals

KW - thiosugars

U2 - 10.1002/adsc.202200557

DO - 10.1002/adsc.202200557

M3 - Article

AN - SCOPUS:85138194099

SN - 1615-4150

VL - 364

SP - 3273

EP - 3282

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 18

ER -

Directed Dehydrogenative Copper-Catalyzed C−H Thiolation in Pseudo-Anomeric Position of Glycals using Thiol and Thiosugar Partners

Résumé

Accès au document

Empreinte digitale

Contient cette citation