What is it about?

This research presents a detailed study of how late transition metals—such as copper, zinc, palladium, and silver—can catalyze the intramolecular hydroamination of alkynes. In this reaction, a nitrogen atom from an amine reacts with a triple bond in the same molecule to form a nitrogen-containing ring, such as pyrrolidines, piperidines, or indoles. These rings are common in pharmaceuticals and functional materials. The study evaluates different metals, ligands, solvents, and anions to identify conditions that make these reactions faster and more efficient. It also provides mechanistic insights and crystallographic data that help explain how the catalysts work and how their structure affects their performance.

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Why is it important?

This work introduces guiding principles for designing effective hydroamination catalysts based on late transition metals. Unlike earlier systems, these catalysts tolerate air and water, making them more practical and robust. The detailed evaluation of ligand and anion effects offers a roadmap for catalyst optimization in C–N bond formation—an essential transformation in organic chemistry. These findings support more sustainable, selective, and tunable approaches to making nitrogen heterocycles, which are key building blocks in medicines and advanced materials.

Perspectives

This was one of my early contributions to catalyst development and a memorable collaboration during my time in Munich. It was especially rewarding to see how combining kinetic analysis, ligand design, and crystallography could lead to a deeper understanding of catalytic performance. The project sharpened my appreciation for how subtle changes in structure and reaction environment influence outcomes—and set the stage for many later studies on selective nitrogen chemistry.

Prof. Dr. Thomas Ernst Müller
Ruhr-Universitat Bochum

Read the Original

This page is a summary of: Developing Transition-Metal Catalysts for the Intramolecular Hydroamination of Alkynes, Organometallics, January 2000, American Chemical Society (ACS),
DOI: 10.1021/om9906013.
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