title: ORGANIC CHEMISTRY. Iron-catalyzed intermolecular [2+2] cycloadditions of unactivated alkenes.
abstract: 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.
authors: Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.
authors: Jordan M
authors: JM
authors: Hoyt
authors: Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.
authors: Valerie A
authors: VA
authors: Schmidt
authors: Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.
authors: Aaron M
authors: AM
authors: Tondreau
authors: Department of Chemistry, Princeton University, Princeton, NJ 08544, USA. pchirik@princeton.edu.
authors: Paul J
authors: PJ
authors: Chirik
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry*; D019281:Dimerization; D007501:Iron / Q000737:chemistry*; D007700:Kinetics; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003503:Cyclobutanes; D008024:Ligands; D007501:Iron