Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides

Molecules. 2019 May 16;24(10):1884. doi: 10.3390/molecules24101884.

Abstract

A convenient Rh(III)-catalyzed C-H activation and cascade [4+2] annulation for the synthesis of naphthalenone sulfoxonium ylides has been developed. This method features perfect regioselectivity, mild and redox-neutral reaction conditions, and broad substrate tolerance with good to excellent yields. Preliminary mechanistic experiments were conducted and a plausible reaction mechanism was proposed. The new type naphthalenone sulfoxonium ylides could be further transformed into multi-substituted naphthols, which demonstrates the practical utility of this methodology.

Keywords: naphthols; rhodium(III); sulfoxonium ylides.

MeSH terms

  • Catalysis
  • Dapsone / analogs & derivatives*
  • Dapsone / chemistry
  • Models, Chemical
  • Molecular Structure
  • Naphthols / chemical synthesis*
  • Naphthols / chemistry
  • Rhodium / chemistry*

Substances

  • Naphthols
  • sulfoxone
  • Dapsone
  • Rhodium