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Palladium-Catalyzed Direct C(sp2)-H ortho-Arylation of Anilides Using 2-Aminophenylpyrazole as the Directing Group
Yuning Shen1, Wan-Chen Cindy Lee1, David A Gutierrez1
1Department of Chemistry, University of San Francisco , 2130 Fulton Street, San Francisco, California 94117, United States.
Abstract:
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.
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