A THREE-COMPONENT CYCLOADDITION OF ALKYL TRIFLUORODIAZOETHANE FOR THE SYNTHESIS OF TRIFLUOROMETHYLATED ISOXAZOLINES

Authors

  • Jingcheng Xu Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, 210037, Nanjing
  • Jiang Liu Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, 210037, Nanjing
  • Haibo Mei Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, 210037, Nanjing
  • Vadim A. Soloshonok Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián IKERBASQUE, Basque Foundation for Science, Plaza Bizkaia, 5, 48011, Bilbao
  • Jianlin Han Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, 210037, Nanjing

DOI:

https://doi.org/10.1007/7268

Keywords:

alkynes, carbene, nitrosoarenes, trifluorodiazoethane, trifluoromethylated isoxazolines, cycloaddition

Abstract

An efficient [2+2+1] cycloaddition reaction of alkyl trifluorodiazoethane with nitrosoarenes and alkynes has been described. This reaction is conducted under mild conditions with CuI as a catalyst in the presence of diisopropylamine, affording a series of trifluoromethylated isoxazolines in up to 96% yield. Furthermore, the reaction tolerates various nitrosoarenes and alkynes and can be applied in large-scale synthesis, which provides an efficient access to trifluoromethylated isoxazolines.

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Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Original Papers