Preparation of Aryl, Alkynyl, and Vinyl Organocopper Compounds by the Oxidative Addition of Zerovalent Copper to Carbon-Halogen Bonds

Article abstract of DOI:10.1021/jo00254a012

A highly reactive copper slurry can be prepared by the reduction of CuI*PEt3 with 1 equiv of lithium naphthalide.The highly reactive copper is found to undergo rapid oxidative addition to alkyl, aryl, alknyl, and vinyl halides under mild conditions.The aryl, alkynyl, and vinyl organocopper compounds are stable at room temperature.These organocopper compounds can bee prepared with variety of functional groups such nitro, nitrile, ester, and ketone.The arylcopper compounds can be cross-coupled in moderate to high yields with acid chlorides and with alkyl-halides.A comparison of different methods for producing activated copper is presented, and the scope and limitations are discussed.