By A. Furstner
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Extra resources for Active Metals [chemistry]
Moreover, these new active copper species could undergo oxidative addition with functionalized alkyl and aryl organic halides to form the corresponding functionalized organocopper reagents at temperatures conducive to the formation of organocopper compounds. Since then many other copper(1) salt complexes have been reduced by preformed lithium naphthalenide. The most common include copper(1) halide phosphine complexes, copper cyanide-lithium halide complexes, and lithium 2-thienylcyanocuprate. The choice of ligand used in preparing the active copper is a critical factor influencing the reactivity of the resulting active copper species.
Another common, although tedious, route to allylic organocopper reagents is the transmetallation of allylic stannanes with an appropriate organocopper reagent, itself derived from a transmetallation of an organolithium or Grignard precursor. Conjugate additions of thienyl-based organocopper reagents to u,b-unsaturated ketones proceed in excellent yields, and these are the organocopper reagents of choice. The addition of TMSCl to the organocopper reagent prior to thc addition of the enone allows the facile formation of the 1,4-conjugate product at -78 "C in excellent isolated yields, as shown in Table 1-25.
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'. The lithium salts are easily removed during aqueous work-up. Howcver, this form of active copper is not as nucleophilic, as evidenced by its inability to undergo epoxide-opening.