Synthesis of α-amino ketones from terminal alkynes via rhodium-catalyzed denitrogenative hydration of N-sulfonyl-1, 2, 3-triazoles

…, T Biyajima, T Fujii, M Murakami

Index: Miura, Tomoya; Biyajima, Tsuneaki; Fujii, Tetsuji; Murakami, Masahiro Journal of the American Chemical Society, 2012 , vol. 134, # 1 p. 194 - 196

Full Text: HTML

Citation Number: 116

Abstract

N-Sulfonyl-1, 2, 3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. An intermediary α-imino rhodium (II) carbenoid undergoes insertion into the O–H bond of water. This transformation formally achieves 1, 2- aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper (I)-catalyzed 1, 3-dipolar cycloaddition with N-sulfonyl azides.