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Synfacts 2020; 16(04): 0439
DOI: 10.1055/s-0040-1707981
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Photocatalytic C–H Alkylation of Quinoxalin-2-ones on a Covalent Organic Framework

Contributor(s):
Yasuhiro Uozumi
,
Shun Ichii
Tian M, Liu S, Bu X, Yu J, Yang X. * Shenyang Normal University, P. R. of China
Covalent Organic Frameworks: A Sustainable Photocatalyst toward Visible-Light-Accelerated C3 Arylation and Alkylation of Quinoxalin-2(1H)-ones.

Chem. Eur. J. 2020;
26: 369-373
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Publication History

Publication Date:
18 March 2020 (online)

 
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Key words

photocatalysis - covalent organic frameworks - hydrazines - quinoxalinones

Significance

A two-dimensional covalent organic framework (2D-COF) catalyzed the alkylation or arylation of quinoxaline-2-ones with alkyl- or arylhydrazines, respectively, under air with blue LED irradiation to give the corresponding C3-alkyl- or -arylquinoxaline-2-ones in ≤89% yield (44 examples). Primary, secondary, and tertiary alkyl and cycloalkyl hydrazines successfully gave the corresponding C3-alkylated products.


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Comment

The authors have previously reported the use of 2D-COF in other photocatalytic reactions (Green Chem. 2019, 21, 2905). In the reaction of 1-methylquinoxalin-2-one with cyclohexylhydrazine hydrochloride, the catalyst was reused five times without significant loss of its activity.


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