Journal of the American Chemical Society, Vol.118, No.15, 3626-3633, 1996
Influences on the Relative Rates for C-N Bond-Forming Reductive Elimination and Beta-Hydrogen Elimination of Amides - A Case-Study on the Origins of Competing Reduction in the Palladium-Catalyzed Amination of Aryl Halides
Typical decomposition by beta-hydrogen elimination has limited the productive catalytic organometallic chemistry of late transition metal amido complexes. However, one reaction that has been shown to involve a late metal amido complex with beta-hydrogens and elude extensive beta-hydrogen elimination is the palladium-catalyzed amination of aryl bromides to give arylamines. The primary side products formed in these catalytic aminations are arenes, the products of aryl halide reduction. It would seem reasonable that both arylamine and arene products result from competitive reductive elimination of amine and beta-hydrogen elimination from a common amido aryl intermediate.
Keywords:METALS