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.