2014European Journal of Organic ChemistryRequires access

A Commercially Available Tantalum Catalyst for the Highly Regioselective Intermolecular Hydroaminoalkylation of Styrenes

Jaika Dörfler, Sven Doye

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Abstract

Abstract The C–C bond‐forming catalytic hydroaminoalkylation of terminal alkenes or styrenes enables a direct and 100 % atom‐efficient synthesis of amines and can generally result in the formation of two regioisomers, the branched and the linear product. Herein, we report that high‐yielding intermolecular hydroaminoalkylation reactions of styrenes can be achieved with excellent regioselectivities in the presence of the commercially available homoleptic catalyst pentakis(dimethylamino)tantalum. In all cases, the branched regioisomer is formed almost exclusively.

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Abstract The C–C bond‐forming catalytic hydroaminoalkylation of terminal alkenes or styrenes enables a direct and 100 % atom‐efficient synthesis of amines and can generally result in the formation of two regioisomers, the branched and the linear product. Herein, we report that high‐yielding intermolecular hydroaminoalkylation reactions of styrenes can be achieved with excellent regioselectivities in the presence of the commercially available homoleptic catalyst pentakis(dimethylamino)tantalum. In all cases, the branched regioisomer is formed almost exclusively.

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Available abstract

Abstract The C–C bond‐forming catalytic hydroaminoalkylation of terminal alkenes or styrenes enables a direct and 100 % atom‐efficient synthesis of amines and can generally result in the formation of two regioisomers, the branched and the linear product. Herein, we report that high‐yielding intermolecular hydroaminoalkylation reactions of styrenes can be achieved with excellent regioselectivities in the presence of the commercially available homoleptic catalyst pentakis(dimethylamino)tantalum. In all cases, the branched regioisomer is formed almost exclusively.

Key concepts: Regioselectivity, Chemistry, Structural isomer, Intermolecular force, Homoleptic, Tantalum, Catalysis, Combinatorial chemistry

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