PREPARATION OF HIGHER-ORDER CYANO AND NON-ATE ALLYL COPPER REAGENTS FROM THE REACTION OF ALLYL CHLORIDES WITH A FORMAL COPPER ANION

The generation of higher order and ''non-ate'' allyl organocopper reag ents have been achieved through the low temperature reaction of allyl chlorides with a formal copper anion. The copper anion is generated vi a the low temperature reduction of Cu(I) complexes by two equivalents of lithium naphthalenide and then oxidatively adds to allyl chlorides with minimal homocoupling. These allyl organocopper reagents undergo s ubstitution reactions with alkyl chlorides and epoxides as well as 1,4 -conjugate addition reactions in good to excellent yields.