Preparation of Higher Order Cyano and "Non-Ate" Allyl Copper Reagents from the Reaction of Allyl Chlorides with a Formal Copper Anion

Article abstract of DOI:10.1016/S0040-4039(00)93380-X

The generation of higher order and "non-ate" allyl organocopper reagents have been achieved through the low temperature reaction of allyl chlorides with a formal copper anion.The copper anion is generated via 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 substitution reactions with alkyl chlorides and epoxides as well as 1,4-conjugate addition reactions in good to excellent yields.