Synthesis of 2-Bromoimidazoles from Alkynes, N-Sulfonylazides, and Bromocyanides

  • Lee, Eunsook
  • Ryu, Taekyu
  • Shin, Eunji
  • Son, Jeong-Yu
  • Choi, Wonseok
  • 외 1명
Citations

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47

초록

A synthetic method for Z-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.

키워드

RHODIUM-CATALYZED TRANSANNULATIONCROSS-COUPLING REACTIONSBOND-FORMING REACTIONSTERMINAL ALKYNESONE-POT1,2,4,5-TETRASUBSTITUTED IMIDAZOLESORGANOMETALLIC CATALYSISCONTROLLING SELECTIVITYC-NPYRROLES
제목
Synthesis of 2-Bromoimidazoles from Alkynes, N-Sulfonylazides, and Bromocyanides
저자
Lee, EunsookRyu, TaekyuShin, EunjiSon, Jeong-YuChoi, WonseokLee, Phil Ho
DOI
10.1021/acs.orglett.5b00977
발행일
2015-05-15
유형
Article
저널명
Organic Letters
17
10
페이지
2470 ~ 2473