Synthesis of N-Arylpyrazoles by Palladium-Catalyzed Coupling of Aryl Triflates with Pyrazole Derivatives

Shunsuke Onodera, Takuya Kochi, Fumitoshi Kakiuchi

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Abstract

A method for the synthesis of N-arylpyrazoles by palladium-catalyzed coupling of aryl triflates with pyrazole derivatives is described. Using tBuBrettPhos as a ligand, the palladium-catalyzed C-N coupling of a variety of aryl triflates including ortho-substituted ones with pyrazole derivatives proceeded efficiently to give N-arylpyrazole products in high yields. 3-Trimethylsilylpyrazole was found to be an excellent pyrazole substrate for the coupling, and the corresponding product, 1-aryl-3-trimethylsilylpyrazole, also served as a great template for the syntheses of N-arylpyrazole derivatives, as demonstrated by regioselective halogenation at the 3-, 4-, and 5-positions of the pyrazole ring.

Original languageEnglish
Pages (from-to)6508-6515
Number of pages8
JournalJournal of Organic Chemistry
Volume84
Issue number10
DOIs
Publication statusPublished - 2019 May 17

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ASJC Scopus subject areas

  • Organic Chemistry

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