Issue 98, 2016
From the journal:

Chemical Communications

Solvent-dependent copper-catalyzed synthesis of pyrazoles under aerobic conditions†

Florian Pünner,ab   Yoshihiro Sohtomeab  and  Mikiko Sodeoka*ab  

* Corresponding authors

a Synthetic Organic Chemistry Laboratory, RIKEN, 2-1, Wako, Saitama 351-0198, Japan
E-mail: sodeoka@riken.jp

b RIKEN Center for Sustainable Resource Science, RIKEN, 2-1, Wako, Saitama 351-0198, Japan

Abstract

We present a copper-catalyzed oxidative cyclization of β,γ-unsaturated hydrazones, utilizing molecular oxygen as a stoichiometric oxidant. The methodology provides distinct classes of pyrazoles simply by changing the reaction solvent. Tris-substituted pyrazoles, having a ketone functionality at the C-5 position, were obtained as the major product in ethanol, while di-substituted pyrazoles were predominantly formed in 1,1,1,3,3,3-hexafluoro-2-propanol.

Graphical abstract: Solvent-dependent copper-catalyzed synthesis of pyrazoles under aerobic conditions

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Article information

DOI
https://doi.org/10.1039/C6CC06935E
Article type
Communication
Submitted
24 Aug 2016
Accepted
25 Oct 2016
First published
25 Oct 2016

Chem. Commun., 2016,52, 14093-14096

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Solvent-dependent copper-catalyzed synthesis of pyrazoles under aerobic conditions

F. Pünner, Y. Sohtome and M. Sodeoka, Chem. Commun., 2016, 52, 14093 DOI: 10.1039/C6CC06935E

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