Synlett 2024; 35(18): 2113-2116
DOI: 10.1055/s-0043-1763749
letter

Expedient Synthesis of gem-CF2-2H-Thiophenes from Enaminothiones

Authors

  • Xinyu Zhang

    a   Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, P. R. of China
  • Xuheng Zhang

    a   Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, P. R. of China
  • Rui Fu

    a   Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, P. R. of China
  • Zhengyu Zhang

    a   Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, P. R. of China
  • Yaojia Jiang

    a   Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, P. R. of China
    b   National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, P. R. of China

The authors gratefully acknowledge funding from the National Natural Science Foundation of China (21971112 and 22361010).


Graphical Abstract

Preview

Abstract

An expedient and easy-to-handle synthetic platform has been established for the constructing of 2H-thiophenes carrying fluorine atoms through [4+1] cyclization of enaminothiones with fluorinated carbene precursors. This simple reaction system is well compatible with a wide range of substrates under completely metal-free conditions. The resulting 2H-thiophenes can undergo further late-stage modifications to yield a wide range of fluorine-substituted heterocycles.

Supporting Information



Publication History

Received: 04 March 2024

Accepted after revision: 25 March 2024

Article published online:
08 April 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany