Christian Bruneau, Mathieu Achard, Zhou Tang, Basker Sundararaju, Zeyneb Sahli, Fan Jiang UMR6226: Institut des Sciences Chimiques de Rennes, Campus de Beaulieu, 35042 Rennes Cedex, France Email: christian.bruneau@univ-rennes1.fr A new class of ruthenium and iridium complexes featuring a bidentate phosphinesulfonate ligand have shown high efficiency in catalytic transformations involving hydrogen transfers. Taking advantage of this reactivity, sequential catalytic processes have been developed for selective N- and sp3C-alkylation to functionalize cyclic amines. Starting from cyclic saturated amines, reactions with alcohols or aldehydes selectively lead to C(3)-substituted cyclic amines with formation of water as sole byproduct. Sequential catalytic transformations initiated by C-N and C-C bond formation involving H-transfer processes followed by cyclization reactions lead to a variety of polycyclic amine derivatives as illustrated in the Scheme. References: B. Sundararaju, M. Achard, G. V. M. Sharma, C. Bruneau, J. Am. Chem. Soc. 2011, 133, 10340-10343. Z. Sahli, B. Sundararaju, C. Bruneau, M. Achard, Green Chem. 2013, 15, 775–779. F. Jiang, K. Yuan, M. Achard, C. Bruneau, Chem.Eur. J. 2013, 19, 10343-10352. F. Jiang, M. Achard, C. Bruneau, Chem. Eur. J. 2015, 21, 14319-14323.

C-N and C-C bond formation via selective functionalization of saturated cyclic amines

254th National Meeting (2017)

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