Pd(II)-catalyzed ortho trifluoromethylation of arenes and insights into the coordination mode of acidic amide directing groups.

Xing-Guo Zhang, Hui-Xiong Dai, Masayuki Wasa, Jin-Quan Yu

Index: J. Am. Chem. Soc. 29th ed., 134 , 11948-11951, (2012)

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Abstract

A Pd(II)-catalyzed trifluoromethylation of ortho C-H bonds with an array of N-arylbenzamides derived from benzoic acids is reported. N-Methylformamide has been identified as a crucial promoter of C-CF(3) bond formation from the Pd center. X-ray characterization of the C-H insertion intermediate has revealed a rare coordination mode of acidic amides as directing groups and the origin of their capacity in directing C-H activation.