Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Palladium-Catalyzed Direct C(sp2)–H ortho-Arylation of Anilides Using 2-Aminophenylpyrazole as the Directing Group

Palladium-Catalyzed Direct C(sp2)–H ortho-Arylation of Anilides Using 2-Aminophenylpyrazole as the Directing Group
David A. Gutierrez, Jie Jack Li, Wan-Chen Cindy Lee, Yuning Shen
Palladium-catalyzed ortho-arylation of anilides was achieved using 2-aminophenyl-1H-pyrazole (2-APP) as a new directing group. Using Pd(OAc)2 as the catalyst and AgO as the promoter, mono- and diarylation of anilides were realized in up to 89% isolated yield. Further manipulation of the arylation product may be accomplished by a 2-step sequence involving an acidic hydrolysis of the methylated amide. More interestingly, in the presence of K2CO3, tandem C–C/C–N cyclization products were obtained for a couple of substrates.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01883

DOI: 10.1021/acs.joc.7b01883

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