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Selective Alkylation of Amines with Alcohols by Cp*-Iridium(III) Half-Sandwich Complexes

Alexander Wetzel, Simone Wöckel, Mathias Schelwies, Marion K. Brinks, Frank Rominger, Peter Hofmann and Michael Limbach*

*CaRLa - Catalysis Research Laboratory, Im Neuenheimer Feld 584, 69120 Heidelberg, Germany, BASF SE, Synthesis & Homogeneous Catalysis, Carl-Bosch-Straße 38, 67056 Ludwigshafen, Germany, Email: michael.limbachbasf.com

A. Wetzel, S. Wöckel, M. Schelwies, M. K. Brinks, F. Rominger, P. Hofmann, M. Limbach, Org. Lett., 2013, 15, 266-269.

DOI: 10.1021/ol303075h (free Supporting Information)


Abstract

Cp*-iridium half-sandwich complexes are highly reactive and selective catalysts for the alkylation of amines with alcohols. [Cp*Ir(Pro)Cl] (Pro = prolinato) is active under mild conditions in either toluene or water without the need for base or other additives, tolerates a wide range of alcohols and amines, and gives secondary amines in good to excellent isolated yields.

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Key Words

secondary amines


ID: J54-Y2013-0170