Copper-Catalyzed Selective Arylation of Nitriles with Cyclic Diaryl Iodonium Salts: Direct Access to Structurally Diversified Diarylmethane Amides with Potential Neuroprotective and Anticancer Activities

Org Lett. 2020 Aug 7;22(15):5789-5795. doi: 10.1021/acs.orglett.0c01829. Epub 2020 Jul 17.

Abstract

A novel, simple, and high-yielding approach for the preparation of diarylmethane amide derivatives has been developed by reacting cyclic diaryl iodonium salts with nitriles using CuCl as a catalyst. The procedure is efficient with high atom economy and a wide substrate range. Importantly, selective arylation of nitriles was obtained without affecting the phenyl amino/hydroxyl groups. Furthermore, two of the diarylmethane amides (3k, 3s) displayed excellent neuroprotective and anticancer activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Amides / pharmacology
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Catalysis
  • Copper / chemistry*
  • Molecular Structure
  • Neuroprotective Agents / chemistry*
  • Neuroprotective Agents / pharmacology
  • Nitriles / chemistry*

Substances

  • Amides
  • Antineoplastic Agents
  • Neuroprotective Agents
  • Nitriles
  • Copper