Alkyl halides alkylmetal coupling

Alkyl halides other than aryl and vinyl halides do not readily undergo oxidative addition with Pd and must, in general, first be converted to alkylmetals. In this connection, however, a recent report on the Ni catalysed selective alkyl-alkyl cross-coupling with Ni(acac)2 and Lil in THF represents a significant breakthrough.34 In cases where the alkyl group contains a p-H atom, reduction of the organic halide via p-dehydropalladation reductive elimination can be a serious side-reaction (Scheme 11.6). 

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