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In contrast, organocopper species derived using triphenylphosphine gave little or no conjugate addition products. The amount of phosphinc ligands present in the reaction mixture has a pronounced effect upon the yield of the conjugate adduct in these reactions. These results are in agreement with those reported by Noyori, in which a significant enhancement in the yields of the conjugate adducts was observed when using excess PBu3 with the organocopper reagents . Chlorotrimethylsilane is also compatible with the reaction conditions .
The zinc is prepared as usual in THF, which is then stripped off and replaced with dry diethyl ether. A one-to-one mixture of aldehyde or ketone and a-bromoester is then added at -5 "C. After stirring for one hour at room temperature the reaction is followed by thc normal work-up procedure r541. Scheme 1-12. Reformatsky reaction. The formation of organozincs from alkyl, aryl, and vinyl bromides or chlorides was formerly possible only by a metathesis reaction of a zinc halide salt with a preformed organolithium or Grignard reagent.
In turn, these allylic organocopper reagents are capable of undergoing cross-coupling reactions with elcctrophilcs such as benzoyl chloride and benzaldehyde to give thc corresponding ketone and alcohol products respectively in good isolated yields, as shown in Table 1-24. Another common, although tedious, route to allylic organocopper reagents is the transmetallation of allylic stannanes with an appropriate organocopper reagent, itself derived from a transmetallation of an organolithium or Grignard precursor.