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

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

Journal of the American Chemical Society (2012-07-12)
Xing-Guo Zhang, Hui-Xiong Dai, Masayuki Wasa, Jin-Quan Yu
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
N-Methylformamide, 99%
Sigma-Aldrich
5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate, 97%
Sigma-Aldrich
5-(Trifluoromethyl)dibenzothiophenium tetrafluoroborate, 97%

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