Aminocarbonylations employing Mo(CO)6 and a bridged two-vial system: allowing the use of nitro group substituted aryl iodides and aryl bromides

J Org Chem. 2012 Dec 21;77(24):11393-8. doi: 10.1021/jo302322w. Epub 2012 Dec 12.

Abstract

A bridged two-vial system aminocarbonylation protocol where Mo(CO)(6) functions as an external in situ solid source of CO has been developed. For the first time both nitro group containing aryl/heteroaryl iodides and bromides gave good to excellent yields in the Mo(CO)(6)-mediated and palladium(0)-catalyzed conversion to benzamides, while the identical one-vessel protocol afforded extensive reduction of the nitro functionality. The above-mentioned bridged two-compartment protocol furnished good results with both primary amines and secondary amines and sluggish aniline nucleophiles at 65-85 °C reaction temperatures.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene / chemistry*
  • Catalysis
  • Halogenation*
  • Ketones / chemistry*
  • Molybdenum / chemistry*
  • Nitro Compounds / chemistry*
  • Palladium / chemistry

Substances

  • Ketones
  • Nitro Compounds
  • hexacarbonylmolybdenum
  • Palladium
  • Molybdenum
  • Benzene