Copper-Catalyzed Oxidative Cross-Dehydrogenative Coupling/Oxidative Cycloaddition: Synthesis of 4‑Acyl-1,2,3-Triazoles

A copper-catalyzed three-component reaction of methyl ketones, organic azides, and various one-carbon (C1) donors was developed that provides 4-acyl-1,2,3-triazoles in moderate to good yields. While DMF, DMA, TMEDA, or DMSO can serve as the C1 donor, best yields were obtained using DMF. The transfor...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-09, Vol.82 (17), p.9198-9203
Main Authors: Liu, Yi, Nie, Gang, Zhou, Zhongzhen, Jia, Lihui, Chen, Yunfeng
Format: Article
Language:English
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Summary:A copper-catalyzed three-component reaction of methyl ketones, organic azides, and various one-carbon (C1) donors was developed that provides 4-acyl-1,2,3-triazoles in moderate to good yields. While DMF, DMA, TMEDA, or DMSO can serve as the C1 donor, best yields were obtained using DMF. The transformation is proposed to proceed via an oxidative C–H/C–H cross-dehydrogenative coupling followed by an oxidative 1,3-dipolar cycloaddition.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01429