Catalytic C-H allylation and benzylation of pyrazoles.

Seri Bae, Ha-Lim Jang, Haeun Jung, Jung Min Joo

The Journal of organic chemistry 2015 Jan 2

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We describe a general approach for the synthesis of allylated and benzylated pyrazoles. An electron-withdrawing substituent, such as nitro, chloro, and ester groups, at C4 renders the Lewis basic nitrogen atom to be less basic and the C-H bond more acidic than the ones of the parent ring, enabling Pd-catalyzed C-H allylation and benzylation reactions of pyrazoles. The new method expanding the scope of the C-H functionalization of pyrazoles beyond arylation reactions provides a rapid access to complex pyrazole compounds.

Citation

Seri Bae, Ha-Lim Jang, Haeun Jung, Jung Min Joo. Catalytic C-H allylation and benzylation of pyrazoles. The Journal of organic chemistry. 2015 Jan 2;80(1):690-7