Synthesis 2004(9): 1497-1503  
DOI: 10.1055/s-2004-822403
PAPER
© Georg Thieme Verlag Stuttgart · New York

MgI2 as an Additive in Ir(I)-Catalyzed Addition of Silylacetylenes to Imines: Expeditious Synthesis of Propargylic Amines

Christian Fischer, Erick M. Carreira*
Laboratorium für Organische Chemie, ETH Hönggerberg, 8093 Zürich, Switzerland
Fax: +41(1)6322830; e-Mail: Carreira@org.chem.ethz.ch;
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Publikationsverlauf

Received 27 April 2004
Publikationsdatum:
08. Juni 2004 (online)

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Abstract

We report a dramatic improvement in the [IrCl(COD)]2-catalyzed addition reaction of silylacetylenes and imines with 2-4 mol% MgI2 as additive. The reaction is very general, with a wide range of imines providing the amine products in excellent yields under convenient reaction conditions. Importantly, the reaction can be conducted with as low as 0.5 mol% catalyst and proceeds in THF as well as in the absence of solvent.

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