Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling

We present a strategy that difunctionalizes unactivated olefins in 1,2-positions with two carbon-based entities. This method utilizes alkyl/arylzinc reagents derived from olefin-tethered alkyl/aryl halides that undergo radical cyclization to generate C­(sp3)-Cu complexes in situ, which are intercepted with aryl and heteroaryl iodides. A variety of (arylmethyl)­carbo- and heterocycles (N, O) can be synthesized with this new method.