Late transition metal-catalyzed directed C-H activation and functionalization allows for the introduction of many important functional groups. The Huo research group has reported a novel Platinum-catalyzed regiospecific acylation of 2-phenoxypyridines with various inexpensive acyl chlorides. To gain further insight and deeper our understanding of the reaction mechanism, many stoichiometric reactions including ligand exchange, cyclometallation, and acylation of platinacycles were studied. Due to the relative high stability of the organoplatinum complexes, stoichiometric reactions can be carried out allowing for the isolation of key intermediates involved in the catalytic cycle. Due to the square planar geometry of the Pt(II) intermediate complexes, there are two possible configurations, the cis and trans isomers. In cases where both isomers were formed, they were separated by column chromatography. When necessary, an independent reaction was performed to synthesize a specific isomer. For example, in order to synthesize the cis coordination compound, a reaction under kinetic control was performed, which involved the reaction of the ligand with K2PtCl4 in a mixture of acetic acid and water at room temperature. All platinum complexes have been characterized by 1H and 13C NMR spectroscopies and elemental analysis. The structures of some key intermediates have been determined using X-ray crystallography.

Synthesis, isolation, and characterization of potential intermediate platinum complexes in Pt-catalyzed C-H acylation reaction

ACS Fall 2021

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