Herein, we present a regioselective Cu-catalyzed oxidative allylic C­(sp3)–H arylation by radical relay using a broad range of heteroaryl boronic acids with inexpensive and readily available unactivated terminal and internal olefins. This C­(sp2)–C­(sp3) allyl coupling has the advantage of using cheap, abundant, and nontoxic Cu2O without the need to use prefunctionalized alkenes, thus offering an alternative method to allylic arylation reactions that employ more traditional coupling partners with preinstalled leaving groups (LGs) at the allylic position.

Herein, we present a regioselective Pd-catalyzed C–H [4 + 2] benzannulation of N-unprotected 3-arylindoles with external readily available 1,3-dienes via an original sequence involving a Pd-catalyzed domino carbopalladation of 1,3-dienes/direct C2–H allylation of an indole ring followed by an oxidation or reduction step. Depending on the nature of the solvent, DCE or CH3CN, two consecutive approaches, oxidative or reductive, have been validated and applied to the design of a novel library of C6-alkyl or (E)-C6-styryl-benzo[c]carbazoles in moderate to good yields.