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Highly Regioselective Au(I)-Catalyzed Hydroamination of Ynamides and Propiolic Acid Derivatives with Anilines

Søren Kramer, Karin Dooleweerdt, Anders Thyboe Lindhardt, Mario Rottländer and Troels Skrydstrup*

*Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Email: tschem.au.dk

S. Kramer, K. Dooleweerdt, A. T. Lindhardt, M. Rottländer, T. Skrydstrup, Org. Lett., 2009, 11, 4208-4211.

DOI: 10.1021/ol901565p (free Supporting Information)


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Abstract

A highly regioselective hydroamination of unsymmetrical electron-poor and electron-rich alkynes with anilines is catalyzed by Au(I) under mild conditions. In addition, applications toward indole syntheses are presented including an example of a one-pot synthesis from a nonfunctionalized aniline.

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Key Words

hydroamination (α-amino nitriles, enamino esters)


ID: J54-Y2009-2760