4.8 Article

Sulfoxonium-Ylide-Directed C-H Activation and Tandem (4+1) Annulation

Journal

ORGANIC LETTERS
Volume 22, Issue 8, Pages 2878-2882

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00451

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Funding

  1. SERB, New-Delhi [EMR/2016/006358]
  2. Indian Institute of Science, R L Fine Chem, Bangalore
  3. SYNMR Chemicals Pvt. Ltd., Bangalore
  4. CSIR, New-Delhi

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Rh(III)-catalyzed C-H activation and cyclization of sulfoxonium ylide with acrylates leads to an efficient synthesis of indanone derivatives. The reaction proceeds under mild and external metal-oxidant-free conditions. The sulfoxonium ylide acts as a traceless directing group as well as an internal oxidant. (4 + 1) Annulation after C-H activation leads to the formation of a carbocyclic ring, and the byproduct obtained is DMSO, which can be easily separated.

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