E-resources
Peer reviewed
-
Hoyt, Jordan M.; Schmidt, Valerie A.; Tondreau, Aaron M.; Chirik, Paul J.
Science (American Association for the Advancement of Science), 08/2015, Volume: 349, Issue: 6251Journal Article
Cycloadditions, such as the 4+2 Diels-Alder reaction to form six-membered rings, are among the most powerful and widely used methods in synthetic chemistry. The analogous 2+2 alkene cycloaddition to synthesize cyclobutanes is kinetically accessible by photochemical methods, but the substrate scope and functional group tolerance are limited. Here, we report iron-catalyzed intermolecular 2+2 cycloaddition of unactivated alkenes and cross cycloaddition of alkenes and dienes as regio- and stereoselective routes to cyclobutanes. Through rational ligand design, development of this base metal–catalyzed method expands the chemical space accessible from abundant hydrocarbon feedstocks.
