Alkylative Dearomatization by Using an Unactivated Aryl Nitro Group as a Leaving Group: Access to Diversified Alkylated Spiro[5.5]trienones
Dong Xia, Xin‐Fang Duan
Abstract
The cleavage of an unactivated aryl nitro group triggered by alkyl radicals enables a dearomative cyclization, affording diversified alkylated spiro[5.5]trienones in good yields. Using readily available compounds (toluene and analogues, alkanes, ethers, ketones, etc.) as alkylating reagents, various alkyls have been implanted into the spirocycles via C(sp3)–H and Ar–NO2 bond activation with high functional group tolerance. This protocol provides a distinct method for the activation of the aryl nitro group.
Topics & Concepts
ChemistryArylAlkylationNitroReagentTolueneAlkylGroup (periodic table)Medicinal chemistryFunctional groupCleavage (geology)RadicalLeaving groupOrganic chemistryCombinatorial chemistryCatalysisEngineeringGeotechnical engineeringPolymerFracture (geology)Catalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques