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Palladium-Catalyzed Intermolecular Directed C−H Amidation of Aromatic Ketones

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posted on 09.02.2011, 00:00 by Bin Xiao, Tian-Jun Gong, Jun Xu, Zhao-Jing Liu, Lei Liu
Pd-catalyzed directed ortho C−H amidation of aromatic ketones with both sulfonamides and amides has been accomplished. The use of an electron-deficient Pd complex, Pd(OTf)2, is crucial for the success of this transformation. Some key intermediates of the reaction, that is, the cyclopalladation complexes of ketones, have been characterized by X-ray crystallography. Experimental analysis of these palladacycles and also the experimental results with N-methyl sulfonamides indicate that the new reaction does not seem to proceed through a nitrene intermediate. The utility of the newly developed reaction was demonstrated for the synthesis of useful organic intermediates such as 2- and 3-alkyl indoles and 2-aminophenyl ketones.