title: An air-tolerant approach to the carbonylative Suzuki-Miyaura coupling: applications in isotope labeling.
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.
authors.affiliation: Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University , Gustav Wieds Vej 14, 8000 Aarhus C, Central Denmark Region, Denmark.
authors.forename: Andreas
authors.initials: A
authors.lastname: Ahlburg
authors.forename: Anders T
authors.initials: AT
authors.lastname: Lindhardt
authors.forename: Rolf H
authors.initials: RH
authors.lastname: Taaning
authors.forename: Amalie E
authors.initials: AE
authors.lastname: Modvig
authors.forename: Troels
authors.initials: T
authors.lastname: Skrydstrup
mesh_terms: D000388:Air; D002247:Carbon Isotopes / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D011345:Fenofibrate / Q000138:chemical synthesis* / Q000737:chemistry; D007553:Isotope Labeling; D015394:Molecular Structure; D003708:Nordazepam / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002247:Carbon Isotopes; D003708:Nordazepam; D002248:Carbon Monoxide; D011345:Fenofibrate