By Furstner A
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C) Yields (70) RCOPh R-X R-R 0 78 -107 -107 -107 -107 -107 -107 -107 -107 - 78 -107 40 77 96 92 33 99 90 93 80 38 61 93 39 12 0 0 0 0 0 0 - Table 1-31. 1,4-Conjugate addition reactions of copper-anion-based organocopper reagents with 2-cyclohexen-1-one. Entry Halide Product Yield (%) 81 3 PhBr 42 4 Br(CH&CI 30 5 Br(CH2)3CN 18 RCOPh - - - - - - - 19 0 - 8 4 sion of the investigations on zero-valent active copper could include a further equivalent reduction of CuOto Cu [4s13d"' + e- = 4s'3d'"] to yield a closed shell anion.
However, the copper anion is a two-equivalent electron reagent, and one equivalent of halide reacts with one equivalent of copper anion.
3 Reactions of Organozinc Reagents with Acid Chlorides Once the organozinc reagent is formed, it easily transmetallates to copper under mild conditions, yielding a highly functionalized cuprate. For example, the organozinc reagent can be added to CuCN . LiBr at -35 "C giving RCu(CN)ZnCl. When reacted with various acid chlorides, this organocopper species gives highly functionalized asymmetrical ketones in high yields. Representative examples of this type of transformation are shown in Table 1-13.