Preparation of new classes of aliphatic, allylic, and benzylic zinc and copper reagents by the insertion of zinc dust into organic halides, phosphates, and sulfonates

The insertion of zinc dust into primary alkyl chlorides, bromides, phosphates, and sulfonates in a polar solvent (DMPU, DMA) and in the presence of a catalytic amount of LiI (0.2 equiv) provides new organozinc reagents of the type RZnX (X=Cl, Br, OSO 2 R, OP(O)(OR) 2 ) in excellent yield. After the transmetalation to the corresponding copper reagent RCu(CN)ZnX using CuCN-1LiCl, the addition of electrophiles, such as Michael acceptors, affords the desired adducts