The Rh(I) and Pd(II) complexes [(η2-C2H4)2Rh(µ-OAc)]2 and Pd(OAc)2 serve as catalyst precursors for the transformation of arenes and olefins to alkenyl arenes in the presence of Cu(II) carboxylate oxidants. A general mechanism for these processes involves arene C–H activation, olefin insertion into the resulting metal-aryl bond, β–hydride elimination, and reaction of the resulting metal-hydride with Cu(II) carboxylate to regenerate the initial catalyst. The presentation will focus on experimental and computational elucidation of the likely active catalyst species, which are proposed to be mixed metal Rh/Cu and Pd/Cu complexes. Also, selectivity differences between Rh(I) and Pd(II) catalytic processes including ortho/meta/para selectivity for substituted arenes and Markovnikov/anti-Markovnikov selectivity for mono-substituted olefins will be discussed.

Comparison of Rh(I) and Pd(II) catalysts for arene alkenylation

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ACS Fall 2022

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