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

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

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.).

Original language	English
Pages (from-to)	3273-3282
Number of pages	10
Journal	Advanced Synthesis and Catalysis
Volume	364
Issue number	18
DOIs	https://doi.org/10.1002/adsc.202200557
Publication status	Published - 20 Sept 2022
Externally published	Yes

Keywords

C−H activation
copper catalysis
directing group
glycals
thiosugars

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10.1002/adsc.202200557

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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",

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doi = "10.1002/adsc.202200557",

language = "English",

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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

Abstract

Keywords

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