A new preparation of highly functionaized aromatic and heteroaromatic zinc and copper organometallics

Abstract

Functionalized aromatic iodides possessing an ester, cyano, chloride or keto group can be converted to arylzinc iodides by reaction with zinc in DMF or DMAC. After transmetallation to the corresponding arylcopper, they react with several electrophiles such as enongs, allylic halides and benzoyl chloride to afford highly functionalized aromatic compounds. Extension to the preparation of polyfunctionalized heteroaromatic zinc iodides and to an alkenylzinc iodide was also successful, although the zinc insertion to a pure (E)-alkenyl iodide furnished an E/Z mixture of alkenyl zinc iodides.