Syntheses of sulfides and selenides through direct oxidative functionalization of C(sp3)-H bond

Org Lett. 2014 Jun 6;16(11):3032-5. doi: 10.1021/ol5011449. Epub 2014 May 16.

Abstract

A new protocol for C-S and C-Se bond formation by the direct functionalization of the C(sp(3))-H bond of alkanes under metal-free conditions was developed. Using (t)BuOO(t)Bu as the oxidant, the reaction of disulfides or diselenides with alkanes gave sulfides or selenides in moderate to good yields. The method was very simple and atom-economical.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrogen Bonding
  • Oxidation-Reduction
  • Selenium Compounds / chemical synthesis*
  • Selenium Compounds / chemistry*
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry*
  • tert-Butylhydroperoxide / chemistry*

Substances

  • Selenium Compounds
  • Sulfides
  • tert-Butylhydroperoxide