Preparation of 5-Aryl-2-Alkyltetrazoles with Aromatic Aldehydes, Alkylhydrazine, Di-tert-butyl Azodicarboxylate, and [Bis(trifluoroacetoxy)iodo]benzene
Taro Imai, Ryo Harigae, Katsuhiko Moriyama and Hideo Togo*
*Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email: togofaculty.chiba-u.jp
T. Imai, R. Harigae, K. Moriyama, H. Togo, J. Org. Chem., 2016, 81, 3975-3980.
DOI: 10.1021/acs.joc.6b00606 (free Supporting Information)
Various 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles were directly prepared in good yields under transition metal-free and mild conditions by the reaction of aromatic aldehydes with methylhydrazine and benzylhydrazine, followed by treatment with di-tert-butyl azodicarboxylate and [bis(trifluoroacetoxy)iodo]benzene in a mixture of dichloromethane and 2,2,2-trifluoroethanol at room temperature.
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