Palladium/XuPhos-Catalyzed Enantioselective Carboiodination of Olefin-Tethered Aryl Iodides

A highly enantioselective palladium-catalyzed iodine atom transfer cycloisomerization of unactivated alkenes has been developed. This represents the first example of highly enantioselective carboiodination of olefin-tethered aryl iodides, which provides a perfect atom economy method to construct a series of optically active 2,3-dihydrobenzofuran, indolines and chromane bearing an alkyl iodide group in moderate to good yields. Moreover, the use of readily available starting materials, a broad substrate scope, high selectivity, mild reaction conditions, as well as versatile transformation of the product make this approach attractive. The mechanism of this Pd(0)-catalyzed asymmetric carboiodination of alkenes has been investigated with density functional theory.