Abstract
Herein, we describe a one-pot protocol for the synthesis of a novel series of polycyclic triazole derivatives. Transition metal-catalyzed decarboxylative CuAAC and dehydrogenative cross coupling reactions are combined in a single flask and achieved good yields of the respective triazoles (up to 97% yield). This methodology is more convenient to produce the complex polycyclic molecules in a simple way.
Highlights
The copper-catalyzed Huisgen [3 + 2] cycloaddition between an organic azide and a terminal alkyne is a well-established strategy for the construction of 1,4-disubstituted 1,2,3-triazoles [1,2,3,4]
The palladium-catalyzed oxidative dehydrogenative coupling reaction may be effected by various oxidants [42,43] such as Ag2O, AgOAc, Ag2CO3, Na2S2O8, Cu(OPiv)2, Cu(OAc)2, benzoquinone and O2 among others
We have chosen a Cu2+ salt because it can be used as an oxidant and as a pre-catalyst for the C–H functionalization and the decarboxylative CuAAC reaction, respectively. 1-(2-Azidophenyl)-1H-benzo[d]imidazole (1a) and phenylpropiolic acid (2a) were selected as model substrates to optimize the reaction conditions
Summary
The copper-catalyzed Huisgen [3 + 2] cycloaddition (or coppercatalyzed azide–alkyne cycloaddition, CuAAC) between an organic azide and a terminal alkyne is a well-established strategy for the construction of 1,4-disubstituted 1,2,3-triazoles [1,2,3,4]. In 2011, Kolarovič et al [6] first reported the copper-catalyzed decarboxylative [3 + 2] cycloaddition reaction of 2-alkynoic acid with organic azides. Lautens et al [41] described a one-pot synthesis of fused triazoles through CuAAC reaction followed by C–H functionalization (Scheme 1). This strategy describes the preparation of fused triazoles by one-pot reaction of 2-alkynoic acid and azide derivatives.
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