4.8 Article

Pd-Catalyzed Spirocyclization via C-H Activation and Benzyne Insertion

Journal

ORGANIC LETTERS
Volume 18, Issue 24, Pages 6324-6327

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03213

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Funding

  1. University of Toronto
  2. Alphora Research, Inc.
  3. Natural Sciences and Engineering Research Council (NSERC)
  4. Ontario Graduate Scholarship

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A palladium-catalyzed spirocyclization forming spirooxindoles and spirodihydrobenzofurans has been achieved. Mechanistic studies suggest that the transformation proceeds through sequential carbopalladation, C-H activation, and benzyne insertion. Both classes of spirocycles have been synthesized in good to excellent yields, and the procedure is readily scalable.

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