Ruthenium-catalyzed [2 + 2] cycloadditions between bicyclic alkenes and alkynyl halides

Karine Villeneuve; Nicole Riddell; Robert W Jordan; Gavin C Tsui; William Tam

doi:10.1021/ol048111g

Ruthenium-catalyzed [2 + 2] cycloadditions between bicyclic alkenes and alkynyl halides

Org Lett. 2004 Nov 25;6(24):4543-6. doi: 10.1021/ol048111g.

Authors

Karine Villeneuve¹, Nicole Riddell, Robert W Jordan, Gavin C Tsui, William Tam

Affiliation

¹ Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.

PMID: 15548071
DOI: 10.1021/ol048111g

Abstract

Ru-catalyzed [2 + 2] cycloadditions between norbornadiene and alkynyl halides were found to occur in moderate to good yields (32-89%). The presence of the halide moiety greatly enhances the reactivity of the alkyne component in the cycloaddition and can be transformed into a variety of products that are difficult or impossible to obtain via direct cycloaddition. [reaction: see text]