An air-tolerant approach to the carbonylative Suzuki-Miyaura coupling: applications in isotope labeling

J Org Chem. 2013 Oct 18;78(20):10310-8. doi: 10.1021/jo401696c. Epub 2013 Sep 26.

Abstract

Carbonylative Suzuki-Miyaura coupling conditions have been developed that proceed without the exclusion of oxygen and in the presence of nondegassed and nondried solvents. By adapting the method to a two-chamber setup, the direct handling of carbon monoxide, produced from stable CO precursors, is avoided. The protocol afforded the desired benzophenones with excellent functional group tolerance and in good yields. Substituting the CO precursor, in the CO-producing chamber, with its carbon-13 labeled version generated the corresponding carbon-13 labeled benzophenones. Finally, the developed system was applied in the synthesis and isotope labeling of two pharmaceuticals, nordazepam and Tricor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Air
  • Carbon Isotopes / chemistry*
  • Carbon Monoxide / chemistry*
  • Catalysis
  • Fenofibrate / chemical synthesis*
  • Fenofibrate / chemistry
  • Isotope Labeling
  • Molecular Structure
  • Nordazepam / chemical synthesis*
  • Nordazepam / chemistry

Substances

  • Carbon Isotopes
  • Nordazepam
  • Carbon Monoxide
  • Fenofibrate