Silver-Catalyzed Activation of Pyridotriazoles for Formal Intramolecular Carbene Insertion into Vinylic C(sp<sup>2</sup>)–H Bonds
Haili Wang, Shaokun Cai, Wenna Ai, Xiufang Xu, Bin Li, Baiquan Wang
Abstract
A silver-catalyzed intramolecular denitrogenative annulation of pyridotriazole with alkene was reported to achieve the challenging carbene insertion into the vinylic C(sp2)–H bond. This protocol has enabled the construction of functionalized 1H-indenes with high efficiency and excellent functional group tolerance. Experimental and computational studies suggest a stepwise mechanism involving a water-promoted hydrogen atom transfer with the aid of a silver catalyst.
Topics & Concepts
ChemistryIntramolecular forceCarbeneCatalysisMedicinal chemistryInsertion reactionFormal synthesisStereochemistryOrganic chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions