4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 17, Pages 9198-9203

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01429

Keywords

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Funding

  1. National Natural Science Foundation of China [21002076, 21441007]
  2. Key Projects of Hubei Provincial Department of Education [D20151502]
  3. Graduate Innovative Fund of Wuhan Institute of Technology [CX2016168]

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

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