Chemoselectivity hydrometallation

Acylation of copper derivatives with acid chlorides works well, but they do not react with free carboxylic acids, unlike the more basic alkyl-lithiums. A dramatic illustration of chemoselectivity comes in the interaction of Bu2CuLi with the free acid 59 and its acid chloride 61. Reaction occurs24 at the alkyl iodide with the one to give 60 and at the acid chloride with the other to give the ketone 62. Acylation can also be achieved by many other metal complexes, from A1 to Zr, but to make those we need hydrometallation, the subject of the next section. 

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