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Published on: June 21, 2017
Conversion of simple alkenes into 1H-1,2,3-triazolium salts by oxidative cycloaddition and subsequent dehydrogenation
Kazuhito Yamakawa1, Yuki Obara1, Yosuke Sumiya2
1Department of Applied Chemistry, Graduate School of Engineering, Chiba Institute of Technology, 2-17-1 Tsudanuma, Narashino, Chiba 275-0016, Japan. haraguchi.ryosuke@p.chibakoudai.jp.
None:
A new method for the synthesis of 1H-1,2,3-triazolium salts from triazenes and simple alkenes has been developed. The oxidative [3+2] cycloaddition of triazenes with alkenes affords 4,5-dihydro-1H-1,2,3-triazolium salts, which undergo dehydrogenative aromatization under remarkably mild conditions (using potassium bicarbonate in air at room temperature) to provide 1H-1,2,3-triazolium salts. This method exhibits broad functional group tolerance and enables the synthesis of a triazolium-based diol, which serves as a cationic diol monomer for cationic polymer synthesis.
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