Research by RWTH Chemists Published in Internationally Esteemed Journal

14/02/2019

A research team headed by Professor Franziska Schoenebeck, Chair of Organic Chemistry I at RWTH Aachen University, has published an article, titled “E-Olefins through intramolecular radical relocation,“ in the January 2019 issue of the prestigious academic journal 'Science.'

  Professor Dr. Franziska Schoenebeck Copyright: RWTH Aachen

Abstract

Controlling the geometry of carbon-carbon double bonds is a central component of chemical manufacturing, especially in the production of pharmaceuticals, food, and fragrances. Even if there are approaches to manufacturing olefins in the preferred trans geometry, they are applicable in special cases only and typically require hydrogen atmosphere as well as expensive metal catalysts.

A useful trick is to shift hydrogen atoms around to selectively interconvert double bond isomers. However, this approach typically requires precious metals.

Schoenebeck and members of her research team now report that nickel, a more abundantly available material, can catalyze rapid conversion of terminal olefins into internal olefins with high selectivity for trans geometry. The odd-electron nickel complex relies on a radical mechanism to shuttle hydrogen to the terminal carbon from the saturated carbon adjacent to the double bond.

This new method may be industrially relevant, as it is easy to apply, scalable, and allows mild conditions and reaction times.

For the full article, please refer to the Science website: E-Olefins through intramolecular radical relocation

Published in:
Science, 25 Jan 2019:
Vol. 363, Issue 6425, pp. 391-396
DOI: 10.1126/science.aav1610