Organophotocatalytic [2+2] Cycloaddition of Electron‐Deficient Styrenes**
Maxim Golfmann, Louis Glagow, Antonios Giakoumidakis, Christopher Golz, Johannes C. L. Walker
Abstract
A visible-light organophotocatalytic [2+2] cycloaddition of electron-deficient styrenes is described. Photocatalytic [2+2] cycloadditions are typically performed with electron-rich styrene derivatives or α,β-unsaturated carbonyl compounds, and with transition-metal-based catalysts. We have discovered that an organic cyanoarene photocatalyst is able to deliver high-value cyclobutane products bearing electron-deficient aryl substituents in good yields. A range of electron-deficient substituents are tolerated, and both homodimerisations and intramolecular [2+2] cycloadditions to fused bicyclic systems are available by using this methodology.
Topics & Concepts
CycloadditionIntramolecular forceCyclobutanePhotocatalysisStyreneBicyclic moleculeChemistryPhotochemistryCatalysisArylElectronMedicinal chemistryCyclobutanesElectron deficiencyStereochemistryOrganic chemistryRing (chemistry)CopolymerPhysicsAlkylPolymerQuantum mechanicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques