Carbon-hydrogen bond functionalization approach for the synthesis of fluorenones and ortho-arylated benzonitriles

A sequence consisting of palladium-catalyzed benzamide ortho-arylation/reaction with (CF3CO)(2)O was developed allowing a convenient one-pot synthesis of ortho-arylated benzonitriles and fluorenone derivatives. The outcome of this transformation is dependent on the amide N-alkyl substituent. Dehydration of ortho-arylated N-cyclohexyl-benzamides by (CF3CO)(2)O results in efficient production of benzonitriles. In contrast, o-arylated N-propylbenzamides are converted to fluorenone derivatives.