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Catalytic C–H Allylation and Benzylation of Pyrazoles

Author:
Bae, Seri, Jang, Ha-Lim, Jung, Haeun, Joo, Jung Min
Source:
Journal of organic chemistry 2015 v.80 no.1 pp. 690-697
ISSN:
1520-6904
Subject:
allylation, arylation, benzylation, carbon-hydrogen bond activation, catalytic activity, chemical bonding, chemical structure, methodology, nitrogen, organic chemistry, palladium, pyrazoles
Abstract:
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.
Agid:
5503563