Directing-Group-Controlled Ring-Opening Addition and Hydroarylation of Oxa/azabenzonorbornadienes with Arenes via C–H Activation
Keyang Zhang, Ruhima Khan, Jingchao Chen, Xuexin Zhang, Yang Gao, Yongyun Zhou, Kangkui Li, Youxian Tian, Baomin Fan
Abstract
An efficient method for the directing group controlled rhodium-catalyzed addition reaction of oxa/azabicylic alkenes with aromatic ketones and benzoic acids has been developed. The ketones and benzoic acids afforded different addition products when reacted with oxa/azabicyclic alkenes. The reaction between ketones and azabenzonorbornadienes furnished the ring-opening addition products. The reaction between benzoic acids and aza/oxabicyclic alkenes proceeded in the absence of silver salt, giving the 1:2 hydroarylation products in yields up to 96%.
Topics & Concepts
ChemistryRing (chemistry)RhodiumBenzoic acidCatalysisSalt (chemistry)Medicinal chemistryGroup (periodic table)Organic chemistryReaction conditionsCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Cross-Coupling Reactions