Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates
Hiroki Yoneyama, Masahiro Numata, Kenji Uemura, Yoshihide Usami and Shinya Harusawa*
*Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara,
Takatsuki, Osaka 569-1094, Japan, Email: harusawa
gly.oups.ac.jp
H. Yoneyama, M. Numata, K. Uemura, Y. Usami, S. Harusawa, J. Org. Chem., 2017, 82, 5538-5556.
DOI: 10.1021/acs.joc.7b00346
see article for more reactions
Abstract
Cyanophosphates (CPs) can be easily prepared from carbonyl compounds, and their reaction with azides provides tetrazoles. A successive termal fragmentation of the tetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous internal and terminal alkynes in good yields under neutral conditions.
see article for more examples
alkyne synthesis developed in this study
Key Words
internal alkynes, terminal alkynes
ID: J42-Y2017
