Synthesis of 2-bromoimidazoles from alkynes, N-sulfonylazides, and bromocyanides.
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.
National Creative Research Initiative Center for Catalytic Organic Reactions, Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea.
Eunsook
E
Lee
National Creative Research Initiative Center for Catalytic Organic Reactions, Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea.
Taekyu
T
Ryu
National Creative Research Initiative Center for Catalytic Organic Reactions, Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea.
Eunji
E
Shin
National Creative Research Initiative Center for Catalytic Organic Reactions, Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea.
Jeong-Yu
JY
Son
National Creative Research Initiative Center for Catalytic Organic Reactions, Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea.
Wonseok
W
Choi
National Creative Research Initiative Center for Catalytic Organic Reactions, Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea.
Phil Ho
PH
Lee