Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

J Am Chem Soc. 2021 Mar 17;143(10):3723-3728. doi: 10.1021/jacs.1c00529. Epub 2021 Mar 3.

Abstract

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Catalysis
  • Nickel / chemistry*
  • Nitriles / chemistry*
  • Sulfides / chemistry*

Substances

  • Biological Products
  • Nitriles
  • Sulfides
  • Nickel