Transition-Metal-Free Arylation and Alkylation of Diarylmethyl p-Tolyl Sulfones with Zinc Reagents

J Org Chem. 2018 Sep 7;83(17):10602-10612. doi: 10.1021/acs.joc.8b01428. Epub 2018 Aug 17.

Abstract

The transition-metal-free synthesis of unsymmetrical and highly functionalized triarylmethanes through arylation of the situ generated o-QMs from diarylmethyl p-tolyl sulfones with aryl zinc reagents is described. Alkyl zinc reagents are also well tolerated in this reaction. Additionally, the straightforward synthesis of the analogue of the antituberculosis agent A and the key precursor of the anti-breast-cancer agent B are achieved by this strategy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Anti-Bacterial Agents / chemistry*
  • Catalysis
  • Hydrocarbons, Aromatic / chemistry*
  • Indicators and Reagents / chemistry
  • Sulfones / chemistry*
  • Zinc / chemistry*

Substances

  • Anti-Bacterial Agents
  • Hydrocarbons, Aromatic
  • Indicators and Reagents
  • Sulfones
  • Zinc