Developing Transition-Metal Catalysts for the Intramolecular Hydroamination of Alkynes
Citations Over TimeTop 10% of 1999 papers
Abstract
Group 7−12 transition-metal complexes serve as effective catalysts for the regioselective intramolecular hydroamination of aminoalkynes having the general formula RC⋮C(CH2)nNH2 (n = 3, R = H, Ph; n = 4, R = H) and of 2-(phenylethynyl)aniline. Primary products are pyrrolidines and piperidines bearing an α-alkylidene functionality and 2-phenylindole, respectively. Isomerization yields the corresponding pyrrolines and 1,2-dehydropiperidines. The catalytic properties of the transition-metal complexes depend on the appropriate choice of ligand, solvent, temperature, and counteranion. Principles for identifying the most active transition-metal catalysts for the hydroamination of alkynes and for optimizing the reaction conditions are developed. The X-ray crystal structure of one catalyst, [PdCl(triphos)](CF3SO3), has been determined.
Related Papers
- → Gold‐Catalyzed Hydroamination of C–C Multiple Bonds(2006)501 cited
- → Tandem Gold(III)‐Catalyzed Amination‐Intramolecular Hydroamination Reactions of 1‐En‐4‐yn‐3‐ols with Sulfonamides: Efficient Approach to Highly Substituted Pyrroles(2008)84 cited
- → A General Study of Aryloxo and Alkoxo Ligands in the Titanium‐Catalyzed Intermolecular Hydroamination of Terminal Alkynes(2005)79 cited
- → Synthesis of 7-Aza-5-deazapurine Analogues via Copper(I)-Catalyzed Hydroamination of Alkynes and 1-Iodoalkynes(2010)30 cited
- Tandem gold(III)-catalyzed amination-intramolecular hydroamination reactions of 1-En-4-yn-3-ols with sulfonamides: efficient approach to highly substituted pyrroles(2008)