Synthesis of acyl carbamates via four component Pd-catalyzed carbonylative coupling of aryl halides, potassium cyanate, and alcohols

Org Lett. 2015 Mar 6;17(5):1248-51. doi: 10.1021/acs.orglett.5b00221. Epub 2015 Feb 13.

Abstract

A simple and mild method is demonstrated for assembling acyl carbamates through a base-free four-component Pd-catalyzed carbonylation of aryl halides in the presence of potassium cyanate and alcohols in a two-chamber system. This approach produces a wide range of aryl acyl carbamates in good to excellent yields from the corresponding aryl bromides or iodides with near-stoichiometric carbon monoxide. In addition, the method can be extended to the synthesis of primary amides thereby expanding the usefulness of cyanate as an ammonia equivalent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Amides / chemistry
  • Ammonia / chemistry
  • Carbamates / chemical synthesis*
  • Carbamates / chemistry
  • Catalysis
  • Cyanates / chemistry*
  • Hydrocarbons, Halogenated / chemistry*
  • Molecular Structure
  • Palladium / chemistry*

Substances

  • Alcohols
  • Amides
  • Carbamates
  • Cyanates
  • Hydrocarbons, Halogenated
  • Palladium
  • Ammonia
  • potassium cyanate