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Extra resources for Active Metals
COCl Rx + 19 16 17 18 15 12 13 14 11 6' 7 8 9 10 5 6 2 3 4 1 Entry Rx Table 1-13. Reactions of organozinc halides mediated by copper with acid chlorides. 3 Rieke Ziti(, 27 includes reactions with "higher order" cuprates as developed by Lipshut/, using 2-thienylcyanocuprate and our highly functionalized organozinc reagents . 2) shows the preparation of a higher order cuprate. LiCu(CN)(2-th) + RZnX + R(2-th)Cu(CN)ZnX (th = thienyl, C4H3S) Unfortunately, we obtained a slightly lower yield together with a small amount (ca.
When compared with other metals produccd by the Rieke method of metal activation, copper suffers from the disadvantage of sintering into larger particlcs, thereby reducing its reactivity. It was apparent that the main difficulty associated with the copper metal \intering was the cxceptionally long reduction time. Previous reports from our laboratory have shown a correlation between particle size and reactivity . It was anticipated that the rcduction of a soluble copper complex would result in a short reduction timc, thereby giving a finely divided coppcr metal.
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. Aryl substrates require excess zinc and occasional refluxing to complete the oxidative addition, owing to thcir reduced reactivity. Di-organozinc bromides and iodides were also prepared and reacted with two equivalents of acid chloride affording the corresponding diketones.
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