4.7 Article

Copper-catalyzed oxidative ipso-carboalkylation of activated alkynes with ethers leading to 3-etherified azaspiro[4.5]trienones

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 1, Issue 5, Pages 484-489

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4qo00006d

Keywords

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Funding

  1. Hunan Provincial Natural Science Foundation of China [13JJ2018]
  2. Natural Science Foundation of China [21172060]
  3. Specialized Research Fund for the Doctoral Program of Higher Education [20120161110041]

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Cu-catalyzed synthesis of 3-etherified azaspiro[4.5]trienones from N-arylpropiolamides and ethers is presented using TBHP oxidant. This is achieved through C(sp(3))-H functionalization, ipso-carbocyclization and dearomatization, and this method represents a new example of alkyne oxidative 1,2-difunctionalization with an ipso-aromatic carbon and a C(sp(3))-H bond by simultaneously forming two new carbon carbon bonds.

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