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Rhodium-catalyzed C-H–CO–olefin Coupling Reactions — A Chelation-assisted Direct Carbonylation At The Ortho C—H Bond In The Benzene Ring Of 2-arylpyridines

Naoto Chatani, Takeshi Uemura, Taku Asaumi, Yutaka Ie, Fumitoshi Kakiuchi, Shinji Murai

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The reaction of 2-arylpyridines with ethylene and carbon monoxide in the presence of a catalytic amount of Rh4(CO)12 results in selective carbonylation at the ortho C—H bond. The reaction is heavily dependent on the solvents used, with DMA (N,N-dimethylacetamide) being the solvent of choice. Steric factors are also important determinants of the efficiency of the reaction.Key words: C—H bond activation, carbonylation, chelation, rhodium, carbon monoxide.