Transition metal-catalyzed, ligand-directed ortho C−H functionalization of arenes has attracted a great deal of attention over the last two decades. A wide variety of groups including alkyl, alkenyl, alkynyl, aryl, halogen, acyl, and acetyloxy groups can be introduced, and many different transition metals have been employed in this catalytic process. However, there has been no report on the use of platinum in those ligand-directed ortho C−H functionalization reactions that can be catalyzed by palladium, ruthenium, rhodium, iridium, and copper, among others. A unique, platinum-catalyzed, direct C−H acylation of 2-(aryloxy)pyridines with acyl chlorides is discovered. The reaction requires neither an oxidant nor other additives. When both ortho positions of the aryl group are accessible, the double acylation occurs readily to produce the diacylated products. Aliphatic, aromatic, and α,β-unsaturated acyl groups can all be introduced. The acylation reaction may proceed through an analogous aromatic electrophilic substitution triggered by the nucleophilic attack of the platinum at the acyl chlorides.<br/>

Platinum catalyzed double acylation of 2-(aryloxy)pyridines via direct C-H activation

255th National Meeting (2018)

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