4.8 Article

Rhodium-Catalyzed Room Temperature C-C Activation of Cyclopropanol for One-Step Access to Diverse 1,6-Diketones

Journal

ORGANIC LETTERS
Volume 22, Issue 7, Pages 2854-2860

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00967

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Funding

  1. NISER
  2. Department of Atomic Energy (DAE)
  3. Council for Scientific and Industrial Research (CSIR), New Delhi [02(0256)/16/EMR II]
  4. Science and Engineering Research Board (SERB), New Delhi [EMRII/2017/001475]

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A rhodium-catalyzed room temperature C-C activation of cyclopropanol has been demonstrated for the single-step synthesis of a range of electronically and sterically distinct 1,6-diketones. This reaction proceeds efficiently in shorter reaction time following a highly atom-economical pathway. To illustrate the synthetic potential of 1,6-diketones, aldol and macrocyclization reactions have been successfully demonstrated. Preliminary mechanistic studies revealed the involvement of nonradical pathways.

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