Active Metals [chemistry] by A. Furstner

By A. Furstner

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Reactions of thienyl-based organocopper reagents with 1,2-epoxybutane. Entry Halide Product Yield (%) 71 60 68 64 78 62 [83]. Both cyclic and acyclic enones worked well with this formulation of active copper. However, more sterically hindered enones, such as isophorone, carvone, and 2,4,4-~imethyl-Zcyclohexen- 1-one, were not amenable for these 1,4-conjugatc additions. The thienyl-based organocopper reagents were also found to be nucleophilic enough to undergo intermolecular epoxide-opening reactions with 1,2-epoxybutane to form single regioisomers in good isolated yields, as shown in Table 1-26.

10) (a) 92 42 70 90 94 81 87 92 82 80 45 81 itics have been prepared. The ability of this CuCN-based active copper to tolerate a wide variety of functionalities allows the facile formation of highly functionalized homoallylic alcohols, lJ,y-unsaturated ketones, and amines in exccllcnt ikolated yields. The organocopper rcagents derived from primary allyl chlorides showed a remarkable themostability with littlc decomposition at 0 OC, unlike sccondary allyl organocopper rcagents, which decompose at a significant rate.

This methodology can be extended to w-alkenyl-sec-alkylzinc reagents as well as the tcrtiary organozinc iodide reagents [62]. 3 Rieke Zinc 31 Rieke Lint can be quite useful in the generation of heteroarylzinc halide reagents. Pyridinylzinc halides can be formed from bromo- or iodopyridines and Rieke zinc at room temperature 1631. These reagents can be cross-coupled with iodobenzene, benzoyl chloride, or benLoic anhydride. The oxidative insertion of Rieke i n c proceeds at room temperature for 2- and 3-indolyl iodides 1641.

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