Three-Component Radical Iodonitrosylative Cyclization of 1,6-Enynes under Metal-Free Conditions
Shaoqun Zhu, Qi Cheng, Hai‐Bo Yang, Xiaoyun Chen, Ying Han, Chao‐Guo Yan, Yaocheng Shi, Hong Hou
Abstract
A three-component, metal-free radical cascade iodonitrosylative cyclization reaction was described. The nitroso radical was generated from tert-butyl nitrite and triggered the radical addition/cyclization/iodination/oxidation sequences. A variety of 1,6-enynes were tested and proved to be compatible, delivering various highly functionalized hetero- and all-carbon cycles and nitro and vinyl C–I bonds containing pyrrolidines, tetrahydrofuran, and cyclopentane in moderate to excellent isolated yields.
Topics & Concepts
ChemistryCyclopentaneTetrahydrofuranRadical cyclizationNitrosoRadicalComponent (thermodynamics)NitroMetalRadical initiatorHalogenationOrganic chemistryCombinatorial chemistrySolventPhysicsAlkylThermodynamicsPolymerPolymerizationOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsVanadium and Halogenation Chemistry