title: Palladium-catalyzed decarboxylative cyanation of aromatic carboxylic acids using [(13)C] and [(14)C]-KCN.
abstract: The development of robust and straightforward methods to efficiently label aromatic moieties starting from simple and convenient radio-synthetic sources still represents a considerable challenge. In this report, a new palladium-catalyzed decarboxylative cyanation protocol has been described. This procedure utilizes [(14)C]-labeled potassium cyanide, one of the simplest and commercially available sources of carbon-14. Under the optimized reaction conditions, a series of [(13)C] and [(14)C]-aromatic nitriles were easily prepared (12-74% yield starting from potassium cyanide). The usefulness of this methodology is highlighted by a rare example of a formal two-step [(12)C]-[(14)C] carbon isotope exchange. The current synthetic approach may represent a promising alternative to traditional preparations of relevant building blocks such as labeled aromatic nitriles.
authors: CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, Gif sur Yvette, F-91191, France.
authors: Olivier
authors: O
authors: Loreau
authors: CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, Gif sur Yvette, F-91191, France.
authors: Dominique
authors: D
authors: Georgin
authors: CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, Gif sur Yvette, F-91191, France.
authors: Frédéric
authors: F
authors: Taran
authors: CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, Gif sur Yvette, F-91191, France.
authors: Davide
authors: D
authors: Audisio
mesh_terms: D002250:Carbon Radioisotopes / Q000737:chemistry*; D002384:Catalysis; D062425:Hydroxybenzoate Ethers / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011190:Potassium Cyanide / Q000737:chemistry*
chemical_list: D002250:Carbon Radioisotopes; D062425:Hydroxybenzoate Ethers; D010165:Palladium; D011190:Potassium Cyanide
keywords: carbon; carbon isotope exchange; cyanation; cyanide; isotopic labeling; palladium catalyzed