How electrophilic are 3-nitroindoles? Mechanistic investigations and application to a reagentless (4+2) cycloaddition
Batoul Rkein, Maxime Manneveau, Ludovik Noël‐Duchesneau, Karine Pasturaud, Muriel Durandetti, Julien Legros, Sami Lakhdar, Isabelle Chataigner
Abstract
)) and reveals unexpected values for aromatic compounds, in the nitrostyrene range. 3-Nitroindoles are sufficiently electrophilic to interact with a common diene namely the Danishefsky's diene at room temperature, in the absence of any activator, to furnish smoothly the dearomatized (4+2) cycloadducts in good yields.
Topics & Concepts
ElectrophileCycloadditionChemistryCombinatorial chemistryComputational chemistryStereochemistryOrganic chemistryCatalysisChemical Reaction MechanismsOrganic Chemistry Cycloaddition ReactionsChemical Reactions and Mechanisms