4.7 Article

Rh(II)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines: switchable reactivity of Rh-azavinylcarbene as [2C]- or aza-[3C]-synthon

Journal

CHEMICAL COMMUNICATIONS
Volume 51, Issue 21, Pages 4507-4510

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cc00268k

Keywords

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Funding

  1. NSFC [21102081, 21272133]
  2. Beijing Natural Science Foundation [2132037]
  3. New Teachers' Fund for Doctor Stations, Ministry of Education [20110002120011]

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The Rh(II)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions.

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