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Synthesis 2011(11): 1783-1791  
DOI: 10.1055/s-0030-1260018
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Peripheral Arylation of 5-Pyrazolones via Enolizable Bond Protection

Hye-Rin Bina,b, Yun Soo Bae*c, Guncheol Kimb, Kee-In Lee*a
a Green Chemistry Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yusong, Taejon 305-600, Korea
Fax: +82(42)8607160; e-Mail: kilee@krict.re.kr;
b Department of Chemistry, College of Natural Science, Chungnam National University, Taejon 305-764, Korea
c Center for Cell Signaling Research, Division of Molecular Life Sciences, Ewha Womans University, Seoul 120-750, Korea
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Publication History

Received 17 February 2011
Publication Date:
28 April 2011 (online)

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Abstract

Peripheral cross-coupling of the enol form of the 5-pyrazolone scaffold with arylboronic acids promoted by [PdCl2(dppf)] afforded the arylated products in good yields. In this coupling, the protection of the enolizable hydroxyl group of pyrazolone is a prerequisite for ensuring the Suzuki-Miyaura cross-coupling. A particular feature of this process is that it enables the synthesis of 5-hydroxy-3-biphenyl and -terphenylpyrazole derivatives with structural diversity.

Key words

Suzuki-Miyaura - tautomers - pyrazolone - peripheral arylation - arylpyrazole

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