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, Email: Carreira
org.chem.ethz.ch
C. Fischer, E. M. Carreira, Synthesis, 2004, 1497-1503.
DOI: 10.1055/s-2004-822403
Abstract
MgI2 as an additive enables a dramatic improvement in the [IrCl(COD)]2-catalyzed addition reaction of silylacetylenes and imines. This general and convenient reaction provides various amine products in excellent yields and can be conducted in THF as well as in the absence of solvent.
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Details
A facile, reliable process for the general preparation of propargylic amines from simple imines and silyl-acetylenes using as low as 0.5 mol% [IrCl(COD)]2 and 2 mol% MgI2 is described. This process is amenable to a wide range of aliphatic and aromatic imines and can be conducted in THF as well as solvent-free. Importantly, the reaction proceeds very cleanly and no workup procedure is necessary. The products are obtained after a simple filtration over silica gel in high yields. Further studies on an asymmetric version are currently being conducted and will be reported in due course.
Key Words
ID: J66-Y2004-2110
