Catalytic direct C-H functionalization is one of the most challenging chemical transformations, which converts unreactive C-H bonds to C-C or C-X (X = a hetero atom) bonds, and has great potential in organic synthesis including synthesis of medicinally or biologically important molecules and building blocks for drug discoveries and developments. A significant progress has been made in the transition metal-catalyzed ligand-directed C-H bond activation and functionalization. Many transition metals have been explored in this promising chemical transformation, and palladium is the most extensively investigated. On the contrary, the use of platinum in the ligand-directed C-H functionalization has received little attention, which might be attributed to generally low activity of platinum catalysts in C-C and C-X bond formation reactions. In this presentation, we will report our recent discovery of a unique platinum-catalyzed ortho-acylation of 2-phenoxypyridine and its analogs. Unlike other metal-catalyzed direct C-H acylation reactions that often require the use of an oxidant or other additives, the platinum-catalyzed reaction requires neither an oxidant nor other additives. The reaction can simultaneously introduce two acyl groups to the ortho positions of the phenyl ring in 2-phenoxypyridine. The reaction mechanism, substituent effects, and the scope of substrates and acylating reagents will be discussed.

Platinum-catalyzed ligand-directed C-H functionalization reactions

253rd National Meeting (2017)

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