The Tortajada Research Group has published a new article in Organometallics titled “Isomerization and Dimerization of 1-Phenylpropyne upon Metalation with Alkyl Lithium Bases and Lewis Basic Polyamine Donors”

The study explores the reactivity of 1-phenylpropyne under metalation conditions, providing insights into isomerization and dimerization processes relevant to organometallic chemistry.

For more information: https://pubs.acs.org/doi/full/10.1021/acs.organomet.5c00490

Abstract

Since the isomerization of C–C multiple bonds is a powerful strategy in organic synthesis, in this study we have investigated the isomerization upon metalation of 1-phenylpropyne with alkyllithium bases in the presence of polydentate amine donors. Combining NMR monitoring and X-ray crystallographic studies, we have found that the terminal alkynylide is formed as the major product, can be isolated, and undergoes dimerization upon heating to selectively form an enyne in high yields.