Organic Letters
Organic Letters
4 years ago

A Regioselective Approach to Trisubstituted Pyrazoles via Palladium-Catalyzed Oxidative Sonogashira-Carbonylation of Arylhydrazines

A Regioselective Approach to Trisubstituted Pyrazoles via Palladium-Catalyzed Oxidative Sonogashira-Carbonylation of Arylhydrazines
Tao Wang, Jiamei Ke, Zhenming Zhang, Junfeng Zhao, Yongliang Tu
A palladium-catalyzed oxidative carbonylation of arylhydrazines and alkynes with balloon pressure CO/O2 to afford trisubstituted pyrazoles in a one-pot manner has been developed. The formation of trisubstituted pyrazoles involves a sequential C–N bond cleavage, carbonylation, Sonogashira coupling, Michael addition, and intramolecular condensation cyclization tandem process. An unprecedented oxidative Sonogashira-carbonylation reaction of arylhydrazine plays a key role for such a facile approach to pyrazoles.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01447

DOI: 10.1021/acs.orglett.7b01447

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