Metal-Free Meerwein Carboarylation of Alkenes with Anilines: A Straightforward Approach to 3-Benzyl-3-alkyloxindoles

A metal-free, straightforward carboarylation reaction of alkenes with anilines was developed that proceeds through a radical C-H cyclization. In the presence of benzoyl peroxide (5 mol-%), tert-butyl nitrite, and an array of anilines, a wide variety of N-arylacrylamides underwent a tandem Meerwein arylation/C-H cyclization to construct the pharmaceutically important 3-benzyl-3-alkyloxindole scaffold in moderate to good yields.