Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1089-1096
doi:10.1351/pac200880051089
First palladium- and nickel-catalyzed oxidative diamination of alkenes: Cyclic urea, sulfamide, and guanidine building blocks*
Kilian Muñiz, Claas H. Hövelmann, Jan Streuff, and Esther Campos-Gómez
Laboratory for Homogeneous Catalysis and Molecular Synthesis, Institute of Chemistry, UMR 7177, Université Louis Pasteur, 4 rue Blaise Pascal, F-67000 Strasbourg Cedex, France
Abstract:
We recently reported the first catalytic diamination of alkenes. This protocol calls for the use of Pd(II) as catalyst in combination with PhI(OAc)2 as terminal oxidant and furnishes the final diamines as cyclic ureas. It consists of an unprecedented two-step reaction of aminopalladation and Csp3-N-bond formation involving a Pd(IV) species. Introduction of Ni(II) catalysts for homogeneous oxidation allows for an efficient diamination with sulfamides, which lead to convenient liberation of the free diamines. In related protocols, the substrate scope of the diamination has been broadened to the formation of cyclic guanidines.
Keywords: catalysis; diamines; homogeneous; nickel; oxidation; palladium.
*Paper based on a presentation at the 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), 2-6 August 2007, Nara, Japan. Other presentations are published in this issue, pp. 807-1194.
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