Copper-Catalyzed One-Pot Synthesis of Functionalized 1,4-Dihydroazete Derivatives from Sulfonyl Azides, Terminal Alkynes, and Tetramethylguanidine
TL;DR: Ketenimine intermediates generated by the addition of copper acetylides to sulfonyl azides are trapped by tetramethylguanidine to afford 1,4-dihydro- N, N -dimethyl-3-aryl(alkyl)-4-aryl(alksyl)sulfoniminoazet-2-amine derivatives in moderate to good yields.
Abstract: Ketenimine intermediates generated by the addition of copper acetylides to sulfonyl azides are trapped by tetramethylguanidine to afford 1,4-dihydro-N,N-dimethyl-3-aryl(alkyl)-4-aryl(alkyl)sulfoniminoazet-2-amine derivatives in moderate to good yields.
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Abstract: Benjamin H. Rotstein,†,‡ Serge Zaretsky,† Vishal Rai,†,§ and Andrei K. Yudin*,† †Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario Canada, M5S 3H6 ‡Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital, and Department of Radiology, Harvard Medical School, 55 Fruit Street, Boston, Massachusetts 02114, United States Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Indore By-pass Road, Bhauri, Bhopal 462 066, MP India
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