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DOI: 10.1055/s-0029-1219722
Copper-Catalyzed Synthesis of Triazolyl-α-CF3-α-Aminophosphonates
D. V. Vorobyeva, N. M. Karimova, T. P. Vasilyeva, S. N. Osipov*, G. T. Shchetnikov, I. L. Odinets, G.-V. Röschenthaler*
A. N. Nesmeyanov Institute of Organoelement Compounds, Moscow, Russia and Jacobs University Bremen gGmbH, Germany
Publication History
Publication Date:
22 April 2010 (online)
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Significance
Reported is the synthesis of acetylenic and propargylic α-CF3-α-aminophosphonates 2 and 3 which are converted into corresponding triazoles 4 and 5 by copper-catalyzed click reactions. Compounds 2 and 3 are obtained in moderate yields from imine 1 by addition of sodium acetylide and Grignard reagent derived from propargyl bromide. The copper(I) species is generated in situ from CuSO4 and sodium ascorbate. The reaction proceeds in moderate to good yields. For aminophosphates 3 the reaction is heated at 80 ˚C resulting in a shorter reaction time (2 h compared to 8-12 h for 2). Selective deprotection of Cbz and pivaloylmethyl groups in good yields as well as the acidolysis of the phosphonate group to the free aminophosphonic acid as a salt was also achieved.