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By A. Furstner

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A second method sometimes employed to prepare Rieke /inc uses a stoichiometric amount of naphthalene with respect to lithium. Both methods yield Rieke zinc with the same reactivity. It should also be noted that the reactivities are similar regardless of the choice of solvent (THF or DME) and that of the halide salt. Further, the electron carrier is not limited to naphthalene. Other carriers such as biphcnyl and anthracene have also been used. 2 Direct Oxidative Addition of Functionalized Alkyl and Aryl Halides Prior to the discovery of Rieke zinc it was not possible to react alkyl, aryl, and vinyl bromides or chlorides directly with zinc.

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. -Unsaturated Ketones These highly functionalized organocopper reagents, derived from the corresponding organozinc.

Also, the rcsulting organocopper reagent was generally more nucleophilic. The general trend of reactivities for phosphine-based copper is P{NMe2)3 > PEt3 > P(CHZNMe2)? > P(cyclohexyl)3 > PBu3 > PPh3 > Diphos > P(OEt)3 as shown in Table 1-21. Phosphites were of little use, but nitrogen-containing phosphine ligands had the advantage that phosphine-containing impurities could be removed by a simplc dilute acid work-up. The active copper prepared utilizing trialkylphosphines, such as PEt3, PBu3 or P(Cy)j, gave 10-30% of homocouplcd products when using alkyl bromides (2 RBr + R-R).

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