Organic Chemistry Portal



Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles

Tomoya Miura, Tsuneaki Biyajima, Tetsuji Fujii and Masahiro Murakami*

*Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan, Email:

T. Miura, T. Biyajima, T. Fujii, M. Murakami, J. Am. Chem. Soc., 2012, 134, 194-196.

DOI: 10.1021/ja2104203


N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion in combination with a copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.

see article for more examples

Key Words

hydrolysis, α-amino ketones, microwave synthesis

ID: J48-Y2012-0080