Amines are of great industrial interest as starting materials or intermediates for the production of fine chemicals and bioactive compounds.[1] The metal-catalyzed alkylation of amines with alcohols via a hydrogen borrowing mechanism has become an outstanding reaction since alcohols are readily available and the only byproduct is water.[2] Although, iridium-based homogeneous catalysts have been reported in this context[3]those systems require harsh reaction conditions and often additives like inorganic bases or silver salts are mandatory for good activity.We will present Cp*-iridium(III) half-sandwich complexes with aminoacidato ligands that are highly active and selective catalysts for the alkylation of amines with alcohols. In contrast to state-of-the-art catalysts, they do not require basic additives or harsh reaction conditions for high activity. They work both in an organic solvent and in water. This opens the door for functionalization of both highly polar and unpolar substrates. Notably, amino acids are inexpensive, non-toxic and readily available ligand precursors underlining the usefulness of the new catalytic system.[1] S. B�hn, S. Imm, L. Neubert, M. Zhang, H. Neumann, M. Beller, ChemCatChem 2011 , 3, 1853.[2] D. Balcells, A. Nova, E. Clot, D. Gnanamgari, R. H. Crabtree, O. Eisenstein, Organometallics 2008 , 27, 2529.[3] See for example: a) K.-i. Fujita, K. Yamamoto, R. Yamaguchi, Org. Lett. 2002 , 4, 2691; b) D. Gnanamgari, E. L. O. Sauer, N. D. Schley, C. Butler, C. D. Incarvito, R. H. Crabtree, Organometallics 2008 , 28, 321; c) A. Prades, R. Corber�n, M. Poyatos, E. Peris, Chem. Eur. J. 2008 , 14, 11474; d) O. Saidi, A. J. Blacker, M. M. Farah, S. P. Marsden, J. M. J. Williams, Chem. Commun. 2010 , 46, 1541; e) R. Kawahara, K.-i. Fujita, R. Yamaguchi, J. Am. Chem. Soc. 2010 , 132, 15108.

Teaching an old dog new tricks: Cp*-iridium(III) half-sandwich complexes with aminoacidato ligands are highly active and selective catalysts in the alkylation of amines with alcohols

245th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.