4.7 Article

Rh(iii)-Catalyzed sequentialortho-C-H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[b,d]pyran-6-ones

Journal

CHEMICAL COMMUNICATIONS
Volume 56, Issue 49, Pages 6688-6691

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc00176g

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Funding

  1. National Natural Science Foundation of China [21602019, 21572025, 21672028, 21971025]
  2. Innovation AMP
  3. Entrepreneurship Talents'' Introduction Plan of Jiangsu Province
  4. Natural Science Foundation of Jiangsu Province [BK20171193]
  5. Jiangsu Key Laboratory of Advanced CatalyticMaterials Technology [BM2012110]
  6. Advanced Catalysis and Green Manufacturing Collaborative Innovation Center

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A rhodium(iii)-catalyzedortho-C-H functionalization of sulfoxonium ylides followed by intramolecular annulation reactions with quinones was described, where the carbonyl in sulfoxonium ylides served as a chelation group. This protocol leads to the efficient formation of 2-hydroxy-6H-benzo[c]chromen-6-one derivatives, proceeding with the cleavage of the C(O)-S bond in sulfoxonium ylides. This protocol featured high chemo-selectivity and functional group tolerance, where sulfoxonium ylides acted as the aroyl sources.

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