PAPER	Synthesis 2004: 1497-1503   DOI: 10.1055/s-2004-822403
© 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;
Received 27 April 2004

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.

Key words

catalysis - imines - acetylene