Active Metals [chemistry] by A. Furstner

By A. Furstner

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5 Copper Cyanide-Based Active Copper Initial attempts to make active copper from CuCN . nLiX complexes (X = Br, C1) met with only limited success. However, exploiting the low-temperature reduction effects seen with other Cu' complexes led to a successful approach for the formation of active copper from CuCN . nLiX [84]. Lowering the reduction temperature to -1 10 "C allowed the active copper solution to react with organic iodides, bromides, and to some extent chlorides, to produce organocopper species in high yields.

NLiX was added into the preformed lithium naphthalenide. It should be noted that the phosphine-based active copper is more reactive than the active copper derived from CuCN . nLiX. rzLiX offers several advantages. First, CuCN is an inexpensive and stable source of Cu' which can be used as received without further purification. Both active copper chemistry and traditional organocopper chemistry involving Cu' have been shown to be effected by the purity of the Cu' used [MI. Second, product isolation is facile and product purity is greatly improved using this phosphinc-free source of Cu'.

Although this species of active copper is not nucleophilic enough to undergo intramolecular or intermolecular epoxide-opening rcactions, the addition of MeLi enhances the nucleophilicity of the allylic organocopper rcagents and allows substitution reactions with epoxides. The MeLi is believed to act as a "dummy" non-transfcrable ligand, presumably forming a higher-order cuprate. Primary and secondary allyl chlorides containing diverse functionalities are tolerated by the CuCN-based copper. -unsaturated ketone, epoxide, nitrile, alkyl acetate, ester, alkyl chloride, and carbamate functionalTable 1-27.

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