Transition-metal-free direct alkylation of aryl tetrazoles via intermolecular oxidative C-N formation

J Org Chem. 2014 Dec 5;79(23):11780-6. doi: 10.1021/jo502283h. Epub 2014 Nov 17.

Abstract

A transition-metal-free synthetic approach for constructing alkylated aryl tetrazoles has been developed using n-Bu4NI as the catalyst and t-BuOOH as the oxidant. It involves the direct C-N bond formation through sp(3) C-H activation. A wide range of benzylic C-H substrates (or alkyl ethers) and aryl tetrazoles undergo this reaction smoothly to deliver the corresponding products in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Benzyl Compounds / chemistry
  • Catalysis
  • Hydrogen Bonding
  • Metals / chemistry*
  • Molecular Structure
  • Oxidants / chemistry*
  • Oxidation-Reduction
  • Tetrazoles / chemical synthesis*
  • Tetrazoles / chemistry
  • Transition Elements / chemistry*

Substances

  • Benzyl Compounds
  • Metals
  • Oxidants
  • Tetrazoles
  • Transition Elements