4.8 Article

C-F Bond Cleavage Enabled Redox-Neutral [4+1] Annulation via C-H Bond Activation

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 5, Pages 1762-1765

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b12142

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Funding

  1. Nanjing Tech University [39837110]
  2. SICAM Fellowship, Jiangsu National Synergetic Innovation Center for Advanced Materials

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Using alpha,alpha-difluoromethylene alkyne as a nontraditional one-carbon reaction partner, a synthetically novel method for the construction of isoindolin-l-one derivatives via Rh(III)-catalyzed [4+1] annulation reaction is reported. The 2-fold C-F bond cleavage not only enables the generation of desired product under an overall oxidant-free condition but also results in a net migration of carbon carbon triple bond. In addition, the present reaction protocol exhibits a tolerance of a wide spectrum of functional groups due to the mild reaction conditions employed.

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