Work

Isomerization and Dimerization of 1-Phenylpropyne upon Metalation with Alkyl Lithium Bases and Lewis Basic Polyamine Donors

Year: 2026

Type: article

Abstract: Being the isomerization of C–C multiple bonds a powerful strategy in organic synthesis, in this study we have inves-tigated the isomerization upon metalation of 1-phenylpropyne with alkyl lithium bases. Combining NMR monitoring and X-Ray crystallographic studies, we have found that in the presence of polydentate amine donors, the terminal alkynylide is formed as the major product of the reaction and that upon heating a dimerization occurs, forming selectively an enyne in high yields.

Source: Organometallics

DOI: 10.1021/acs.organomet.5c00490

Authors: Mikaël Le Roch, Aurélien Crochet, Andreu Tortajada

Institution: University of Fribourg

Language: English

Topic: Coordination Chemistry and Organometallics

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung, Université de Fribourg

Awards: Unlocking Low-valent First-row Transition Metals for Catalytic Cycloaddition Reactions, Design and Synthesis of New Biorenewable Jet Fuels Using Alkali-Metal Amides