Abstract
Cycloadditions of azides with alkynes to form triazoles under thermal conditions (Huisgen cycloaddition)[1] or in the presence of copper [click reaction, copper-catalyzed azide–alkyne cycloaddition (CuAAC)][2,3] are reactions of fundamental importance in organic chemistry. Triazoles can also be obtained by means of ruthenium,[4] silver,[5] and iridium[6] catalysis, as well as by a zinc-mediated process.[7] In sharp contrast, very different reactivity has been observed in the reaction of terminal alkynes with TMSN3 in the presence of group 11 metal salts and complexes.[8] Thus, the group of Jiao recently made the remarkable observation that alkynes (1; R=alkyl, aryl, alkenyl) react with TMSN3 in the presence of Ag2CO3 as catalyst to form nitriles (2; Scheme 1).[9] The same group has reported the cleavage of the aryl–alkyne C(sp2)=C(sp) bond of alkynes (1) using [Au(PPh3)Cl] and AgCO3 in the presence of H2O and trifluoroacetic acid (TFA) to form carboxamides.[10]
Published Version
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