4.5 Article

Copper Acetate Catalyzed Regioselective Synthesis of Substituted 1,2,3-Triazoles: A Versatile Azide-Alkene Cycloaddition/Oxidation Approach

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 4, Pages 847-854

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201501301

Keywords

Nitrogen heterocycles; Cycloaddition; Regioselectivity; Alkenes; Azides; Copper

Funding

  1. Council of Scientific and Industrial Research (CSIR), New Delhi [02/0180/14/EMR-II]
  2. Department of Science and Technology - Fund for Improvement of Science and Technology (DST-FIST), India
  3. Ministry of Human Resource Development (MHRD), India

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A copper acetate catalyzed oxidative cycloaddition reaction of benzyl and aryl azides with terminal and internal olefins that contain electron-withdrawing groups (COOR, CONH2, CN, CHO, COR) has been developed. The reaction employs air as the oxidant and does not require any base or additives to afford 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles in good to excellent yields with high regioselectivity.

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