title: Copper-mediated sequential cyanation of aryl C-B and arene C-H bonds using ammonium iodide and DMF.
abstract: The cyanation of aromatic boronic acids, boronate esters, and borate salts was developed under copper-mediated oxidative conditions using ammonium iodide and DMF as the source of nitrogen and carbon atom of the cyano unit, respectively. The procedure was successfully extended to the cyanation of electron-rich benzenes, and regioselective introduction of a cyano group at the arene C-H bonds was also achieved. The observation that the reaction proceeds via a two-step process, initial iodination and then cyanation, led us to propose that ammonium iodide plays a dual role to provide iodide and nitrogen atom of the cyano moiety.
authors.affiliation: Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, Republic of Korea.
authors.forename: Jinho
authors.initials: J
authors.lastname: Kim
authors.forename: Jiho
authors.initials: J
authors.lastname: Choi
authors.forename: Kwangmin
authors.initials: K
authors.lastname: Shin
authors.forename: Sukbok
authors.initials: S
authors.lastname: Chang
mesh_terms: D001881:Borates / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D004126:Dimethylformamide; D004952:Esters / Q000737:chemistry*; D005559:Formamides / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001881:Borates; D001897:Boronic Acids; D004952:Esters; D005559:Formamides; D007454:Iodides; D009570:Nitriles; D000644:Quaternary Ammonium Compounds; D003300:Copper; D004126:Dimethylformamide