title: Reductive carbonylation of aryl halides employing a two-chamber reactor: a protocol for the synthesis of aryl aldehydes including 13C- and D-isotope labeling.
abstract: A protocol has been developed for conducting the palladium-catalyzed reductive carbonylation of aryl iodides and bromides using 9-methylfluorene-9-carbonyl chloride (COgen) as a source of externally delivered carbon monoxide in a sealed two-chamber system (COware), and potassium formate as the in situ hydride source. The method is tolerant to a wide number of functional groups positioned on the aromatic ring, and it can be exploited for the isotope labeling of the aldehyde group. Hence, reductive carbonylations run with (13)COgen provide a facile access to (13)C-labeled aromatic aldehydes, whereas with DCO2K, the aldehyde is specifically labeled with deuterium. Two examples of double isotopic labeling are also demonstrated. Finally, the method was applied to the specific carbon-13 labeling of the β-amyloid binding compound, florbetaben.
authors.affiliation: Center for Insoluble Protein Structures (InSPIN), Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark.
authors.forename: Signe
authors.initials: S
authors.lastname: Korsager
authors.forename: Rolf H
authors.initials: RH
authors.lastname: Taaning
authors.forename: Anders T
authors.initials: AT
authors.lastname: Lindhardt
authors.forename: Troels
authors.initials: T
authors.lastname: Skrydstrup
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis*; D000814:Aniline Compounds / Q000737:chemistry*; D002247:Carbon Isotopes / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry; D002384:Catalysis; D003903:Deuterium / Q000737:chemistry; D005449:Fluorenes / Q000737:chemistry*; D005561:Formates / Q000737:chemistry; D007553:Isotope Labeling; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013267:Stilbenes / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000814:Aniline Compounds; D002247:Carbon Isotopes; D005449:Fluorenes; D005561:Formates; D013267:Stilbenes; D010165:Palladium; D002248:Carbon Monoxide; D003903:Deuterium; C527756:4-(N-methylamino)-4'-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)stilbene