ChemInform Abstract: Palladium-Catalyzed Direct Arylation of 5-Chloropyrazoles: A Selective Access to 4-Aryl Pyrazoles.

Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS- Université de Rennes "Organométalliques: Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France.
The Journal of Organic Chemistry (Impact Factor: 4.72). 07/2012; 77(17):7659-64. DOI: 10.1021/jo301047v
Source: PubMed


The use of a temporary protection by a chloro group at C5 of pyrazoles allows the synthesis of the 4-arylated pyrazoles, which were previously inaccessible by palladium-catalyzed direct arylation, with complete regioselectivity and in high yields using in most cases as little as 0.5-0.1 mol % Pd(OAc)(2) as the catalyst with electron-deficient aryl bromides. Moreover, from 5-chloro-1,3-dimethylpyrazole, sequential catalytic C4 arylation, dechlorination, catalytic C5 arylation reactions allowed the synthesis of a 4,5-diarylated pyrazole derivative.

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Available from: Lu Chen, Feb 07, 2015
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