Directed copper-catalyzed dehydrogenative C-H amination of unsaturated sialic acids

Linlin Li; Angélique Ferry; Samir Messaoudi

doi:10.1039/d3qo01448g

Directed copper-catalyzed dehydrogenative C-H amination of unsaturated sialic acids

Linlin Li
, Angélique Ferry
, Samir Messaoudi

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

Abstract

This study reports the first example of a Cu-catalyzed dehydrogenative C(sp²)-H amination of sialyl glycals. The scope of this reaction is demonstrated by the use of a variety of substituted azole nucleophiles. This approach offers an efficient entry to an unknown chemical space related to N-branched sialyl glycals. Additionally, removal of the directing group and further post functionalizations on the azole nucleus could also be realized by different cross-coupling processes.

Original language	English
Pages (from-to)	466-471
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	11
Issue number	2
DOIs	https://doi.org/10.1039/d3qo01448g
Publication status	Published - 27 Nov 2023
Externally published	Yes

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title = "Directed copper-catalyzed dehydrogenative C-H amination of unsaturated sialic acids",

abstract = "This study reports the first example of a Cu-catalyzed dehydrogenative C(sp2)-H amination of sialyl glycals. The scope of this reaction is demonstrated by the use of a variety of substituted azole nucleophiles. This approach offers an efficient entry to an unknown chemical space related to N-branched sialyl glycals. Additionally, removal of the directing group and further post functionalizations on the azole nucleus could also be realized by different cross-coupling processes.",

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AU - Messaoudi, Samir

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Y1 - 2023/11/27

N2 - This study reports the first example of a Cu-catalyzed dehydrogenative C(sp2)-H amination of sialyl glycals. The scope of this reaction is demonstrated by the use of a variety of substituted azole nucleophiles. This approach offers an efficient entry to an unknown chemical space related to N-branched sialyl glycals. Additionally, removal of the directing group and further post functionalizations on the azole nucleus could also be realized by different cross-coupling processes.

AB - This study reports the first example of a Cu-catalyzed dehydrogenative C(sp2)-H amination of sialyl glycals. The scope of this reaction is demonstrated by the use of a variety of substituted azole nucleophiles. This approach offers an efficient entry to an unknown chemical space related to N-branched sialyl glycals. Additionally, removal of the directing group and further post functionalizations on the azole nucleus could also be realized by different cross-coupling processes.

U2 - 10.1039/d3qo01448g

DO - 10.1039/d3qo01448g

M3 - Article

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SP - 466

EP - 471

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 2

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Directed copper-catalyzed dehydrogenative C-H amination of unsaturated sialic acids

Abstract

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