title: Palladium catalysed aryl amination reactions in supercritical carbon dioxide.
abstract: Palladium catalysed C-N bond formation in supercritical carbon dioxide has been accomplished. Carbamic acid formation is avoided in part through the use of an N-silylamine as the coupling partner. Employing a catalyst system of Pd2dba3(1 mol%) and 2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl (X-Phos)(2 mol%) enabled the catalytic amination of aryl bromides and chlorides with N-silylanilines to be realised in excellent yield. Extension of the methodology to the N-arylation of N-silyldiarylamines, N-silylazoles and N-silylsulfonamides is reported.
authors.affiliation: Melville Laboratory, Department of Chemistry, Lensfield Road, Cambridge, UKCB2 1EW.
authors.forename: Catherine J
authors.initials: CJ
authors.lastname: Smith
authors.forename: Melanie W S
authors.initials: MW
authors.lastname: Tsang
authors.forename: Andrew B
authors.initials: AB
authors.lastname: Holmes
authors.forename: Rick L
authors.initials: RL
authors.lastname: Danheiser
authors.forename: Jefferson W
authors.initials: JW
authors.lastname: Tester
mesh_terms: D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002245:Carbon Dioxide / Q000737:chemistry*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011312:Pressure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D006841:Hydrocarbons, Aromatic; D012821:Silanes; D002245:Carbon Dioxide; D010165:Palladium