Copper-Catalyzed Alkylarylation of Unactivated Alkenes: Synthesis of 3-Alkyl Indolines from N-Allyl Anilines and Alkanes.

A rare example of C(sp3 )-H functionalization of simple alkanes with unactivated alkenes is presented. In the presence of a copper salt and di-tert-butyl peroxide (DTBP), N-allyl anilines underwent exo-selective alkylation/cyclization cascade with unactivated alkenic bonds as radical acceptors and simple alkanes as radical precursors, providing a direct access to 3-alkyl indolines. The present protocol features simple operation, broad substrate scope and great exo selectivity.