Environmentally Benign and User-Friendly <i>In Situ</i> Generation of Nitrile Imines from Hydrazones for 1,3-Dipolar Cycloaddition
Liyan Song, Yunrong Lai, Hongzuo Li, Jipeng Ding, Hongliang Yao, Su Qian, Binbin Huang, Ming‐An Ouyang, Rongbiao Tong
Abstract
Nitrile imines are highly reactive and versatile dipoles and conventionally generated in situ from unstable hydrazonyl halides under basic conditions. Herein, we report the first green and user-friendly protocol for in situ generation of nitrile imines from Oxone–KBr oxidation of hydrazones and base-promoted dehydrobromination. The nitrile imines were demonstrated for 1,3-dipolar cycloaddition with various dipolarophiles, including alkene and alkyne groups. With its green nature, ease of operation, and air and moisture tolerance, we expect our method will find wide applications in organic synthesis.
Topics & Concepts
NitrileIn situ1,3-Dipolar cycloadditionEnvironmentally friendlyUser FriendlyCycloadditionDipoleChemistryComputer scienceOrganic chemistryCombinatorial chemistryProgramming languageBiologyEcologyCatalysisCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis