Alkylative Dearomatization by Using an Unactivated Aryl Nitro Group as a Leaving Group: Access to Diversified Alkylated Spiro[5.5]trienones

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.