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  • Title: Palladium catalysed aryl amination reactions in supercritical carbon dioxide.
    Author: Smith CJ, Tsang MW, Holmes AB, Danheiser RL, Tester JW.
    Journal: Org Biomol Chem; 2005 Oct 21; 3(20):3767-81. PubMed ID: 16211113.
    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.
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