Synthesis 2005(7): 1200-1204  
DOI: 10.1055/s-2004-834863
PSP
© Georg Thieme Verlag Stuttgart · New York

Regioselective Preparation of 2-Phenylethylamines from 1-Phenyl-2-alkyl­alkynes by Hydroamination/Reduction Sequences

Andreas Heutling, René Severin, Sven Doye*
Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Fax: +49(6221)544205; e-Mail: sven.doye@urz.uni-heidelberg.de;
Further Information

Publication History

Received 27 July 2004
Publication Date:
21 October 2004 (eFirst)

Abstract

Ind2TiMe2 is a highly active and general catalyst for the intermolecular hydroamination of alkynes. Particularly impressive is that Ind2TiMe2 makes it possible to perform hydroamination reactions of unsymmetrically substituted 1-phenyl-2-alkylalkynes with primary aryl-, tert-alkyl-, sec-alkyl-, and n-alkylamines in a highly regioselective fashion. Since the initially formed imines can easily be reduced with zinc-modified NaBH3CN, 2-phenylethylamines are accessible in reliable one-pot procedures from 1-phenyl-2-alkylalkynes and primary amines on a 10 mmol scale.

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