DIRECT COUPLING OF FUNCTIONALIZED ORGANOLITHIUM COMPOUNDS WITH ARYL AND VINYL HALIDES

The reaction between beta- and gamma-nitrogen-functionalized and gamma - and epsilon-oxygen-functionalized organolithium compounds 3, 4, 30-3 2 and different aromatic, heteroaromatic, and vinylic halides affords directly the corresponding substitution products: functionalized benza mides 5-26 and alcohols 33-37. Symmetrical and mixed products of doubl e coupling 38-40 were also prepared from 1,4-diiodobenzene. The format ion of alkyl halides as intermediates has been verified. Aryl or vinyl halides giving rise to unstable aryl or vinyllithium reagents were un successful in the coupling reaction.