Regioselective Synthesis of Naphthothiophenes by Pd Catalyzed Cross-Coupling Reactions and Alkyne-Carbonyl Metathesis

J Org Chem. 2022 Apr 1;87(7):4560-4568. doi: 10.1021/acs.joc.1c02838. Epub 2022 Mar 11.

Abstract

Naphthothiophenes were prepared from commercially available 2,3-dibromothiophenes in two steps by one-pot Suzuki/Sonogashira or Sonogashira/Suzuki coupling reactions, followed by intramolecular alkyne-carbonyl-metathesis reactions. The final cyclization reaction proceeds in the presence of p-toluenesulfonic acid and provides a rapid access to two series of isomeric naphthothiophenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes*
  • Catalysis
  • Cyclization
  • Palladium*

Substances

  • Alkynes
  • Palladium