Ultrasound promoted Barbier reactions and Csp3-Csp2 Stille coupling for the synthesis of diarylmethanes and substituted benzophenones

Ultrason Sonochem. 2013 Jan;20(1):40-6. doi: 10.1016/j.ultsonch.2012.06.014. Epub 2012 Jul 7.

Abstract

Here we present the preparation of a variety of diarylmethanes obtained via ultrasound Stille coupling under palladium catalysis between some substituted aryl compounds and benzyltributyltin compounds generated through sonicated Barbier reaction in a very short time reaction and excellent yield. The study reported below compares different methods to optimize the synthesis of usually unstable benzyltin derivatives and is another contribution to the investigation of Csp(3)-Csp(2) coupling process involving benzyl-aryl reagents. Substituted carboxylated benzophenones were easily prepared in a very good yield by oxidation of some diarylmethanes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry*
  • Benzophenones / chemical synthesis*
  • Benzophenones / chemistry*
  • Chemistry Techniques, Synthetic
  • Methane / chemical synthesis*
  • Methane / chemistry*
  • Ultrasonics*

Substances

  • Anti-Bacterial Agents
  • Benzophenones
  • Methane