Journal of the American Chemical Society, Vol.134, No.1, 194-196, 2012
Synthesis of alpha-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles
N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce alpha-amino ketones in high yield. An intermediary alpha-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.