Cyclization of Vinyl Diazo Compounds with Benzofuran-Derived Azadienes Enabled by NaBAr<sup>F</sup><sub>4</sub>
Ting Yang, Qin Jiang, Chunmei Wang, Song-Liang Li, Cheng‐Yu He, Wen‐Dao Chu, Quan‐Zhong Liu
Abstract
An unprecedented cycloaddition of vinyl diazo compounds with benzofuran-derived azadienes catalyzed by rarely independently used NaBAr F 4 has been established. Benzofuran-fused hydropyridines were constructed with excellent yields and high diastereoselectivity via a Na + -catalyzed inverse-electron-demand aza-Diels–Alder reaction. Notably, this transformation also features good compatibility with a one-pot protocol to deliver the spiro[benzofuran-cyclopentene] skeleton, as well as perfect atom economy and simple reaction conditions.
Topics & Concepts
BenzofuranCycloadditionChemistryDiazoCatalysisCombinatorial chemistryCyclopenteneMedicinal chemistryOrganic chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions