Site‐Selective Alkenylation of Unactivated C(sp<sup>3</sup>)−H Bonds Mediated by Compact Sulfate Radical
Mitsuhiro Ueda, Kazuya Kamikawa, Takahide Fukuyama, Yi‐Ting Wang, Yen‐Ku Wu, Ilhyong Ryu
Abstract
Abstract A broad variety of unactivated acyclic and alicyclic substrates cleanly undergo site‐selective alkenylation of unactivated C(sp 3 )−H bonds with 1,2‐bis(phenylsulfonyl)ethene in the presence of persulfate. This simple transformation furnishes ( E )‐2‐alkylvinylphenylsulfones in up to 88 % yield. In contrast with the previously reported decatungstate protocol, the current method is applicable to alkenylation of sterically hindered C−H bonds. This important advantage significantly broadens the substrate scope, and is attributed to the compact size of the sulfate radical employed in the C−H activation and cleavage.
Topics & Concepts
Alicyclic compoundChemistrySteric effectsYield (engineering)Medicinal chemistrySubstrate (aquarium)Bond cleavageCleavage (geology)PersulfateStereochemistryPhotochemistryOrganic chemistryCatalysisMaterials scienceComposite materialMetallurgyGeologyOceanographyFracture (geology)Sulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions