Synthesis of 2-bromoimidazoles from alkynes, N-sulfonylazides, and bromocyanides
Eunsook Lee1, Taekyu Ryu1, Eunji Shin1
1National Creative Research Initiative Center for Catalytic Organic Reactions, Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea.
Abstract:
A synthetic method for 2-bromoimidazoles is developed from Rh-catalyzed cyclization of N-sulfonyl-1,2,3-triazoles with bromocyanides. Cu-catalyzed [3 + 2] cycloaddition followed by Rh-catalyzed cyclization starting from alkynes, N-sulfonylazides, and bromocyanides is also demonstrated for de novo synthesis of 2-bromoimidazoles in one pot. Moreover, this work was successfully employed to introduce diverse functional groups to the 2-position of imidazoles via cross-coupling reaction.
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