Transition‐Metal‐Free Intermolecular Hydrocarbonation of Styrenes Mediated by NaH/1,10‐Phenanthroline
Kanako Nozawa‐Kumada, So Onuma, Kanako Ono, Tomohiro Kumagai, Yuki Iwakawa, Katsuhiko Sato, Masanori Shigeno, Yoshinori Kondo
Abstract
A transition-metal-free intermolecular coupling reaction of halocompounds with styrenes in the presence of NaH and 1,10-phenanthroline was developed. This reaction afforded hydrocarbonated products with complete anti-Markovnikov selectivity. The method allows the use of a wide range of halocompounds, including aryl and alkyl halides, and good functional group tolerance. Detailed mechanistic studies indicated that an anilide anion generated in situ by the NaH-mediated reduction of 1,10-phenanthroline works as an electron donor and a hydrogen source.
Topics & Concepts
PhenanthrolineChemistryIntermolecular forceArylAlkylMarkovnikov's ruleHalideSelectivityFunctional groupMedicinal chemistryPolymer chemistryCombinatorial chemistryCatalysisOrganic chemistryMoleculeRegioselectivityPolymerCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms