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Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives

Anders Lindhardt Hansen and Troels Skrydstrup*

*Department of Chemistry and the Interdisciplinary Nanoscience Center, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark, Email: tschem.au.dk

A. L. Hansen, T. Skydstrup, J. Org. Chem., 2005, 70, 5997-6003.

DOI: 10.1021/jo050669u (free Supporting Information)


Abstract

Highly regioselective and efficient Heck reactions of aryl triflates with N-acyl-N-vinylamines were achieved using Pd2(dba)3, dppf, and diethylisopropylamine in dioxane. The coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketones or in situ hydrogenation in the presence of (Ph3P)3RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of benzylic amines.

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Key Words

Heck Reaction, Benzylic Amines, Aryl Ketones


ID: J42-Y2005-880