Direct formation and reaction of thienyl-based organocopper reagents

The preparation of a highly reactive zerovalent copper complex by the direct reduction of lithium (2-thienylcyano)cuprate with preformed lithium naphthalenide is described. This active copper species oxidatively adds to carbon-halogen bonds to form organocopper reagents. The ability to directly form the organocopper reagent from organic tides and active copper allows for the incorporation of a wide variety of functionalities to be present in the organic tides and the organocopper reagents. Significantly, this formulation of active copper was able to oxidatively add to allyl chlorides and acetates at low temperatures to allow the direct formation of allylic organocopper reagents without Wurtz-type homocoupling