Recent Progress on the Application of CF3-Imidoyl Sulfoxonium Ylides in Annulation Reactions

doi:10.6023/cjoc202502027

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (8): 2796-2814.DOI: 10.6023/cjoc202502027 Previous Articles Next Articles

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CF₃-亚胺酰基亚砜叶立德在环化反应中的应用研究进展

陈晓培^a^,^†^,^*(), 王清龙^a^,^†, 侯学会^a, 王川川^a, 马志伟^a, 张京玉^b^,^*()

^a 河南牧业经济学院理学部郑州 450046
^b 河南中医药大学药学院郑州 450046

收稿日期:2025-02-22 修回日期:2025-03-29 发布日期:2025-05-06
作者简介:
†共同第一作者.
基金资助:
河南省科技攻关(242102111109); 河南省科技攻关(242102320263); 河南省科技攻关(252102110213); 河南省科技攻关(252102110013)

Recent Progress on the Application of CF₃-Imidoyl Sulfoxonium Ylides in Annulation Reactions

Xiaopei Chen^a^,^*(), Qinglong Wang^a, Xuehui Hou^a, Chuanchuan Wang^a, Zhiwei Ma^a, Jingyu Zhang^b^,^*()

^a Faculty of Science, Henan University of Animal Husbandry and Economy, Zhengzhou 450046
^b School of Pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou 450046

Received:2025-02-22 Revised:2025-03-29 Published:2025-05-06
Contact: *E-mail:chenxp@hnuahe.edu.cn;jyzhang2004@126.com
About author:
†These authors contributed equally to this work.
Supported by:
Key Scientific and Technological Project of Henan Province(242102111109); Key Scientific and Technological Project of Henan Province(242102320263); Key Scientific and Technological Project of Henan Province(252102110213); Key Scientific and Technological Project of Henan Province(252102110013)

CF₃-imidoyl sulfoxonium ylides represent a significant class of nitrogen-containing trifluoromethylated synthons. These compounds not only function as versatile dipoles in cascade annulation but also serve as efficient carbene precursors via C—H bond activation/annulation for constructing diverse trifluoromethyl-decorated cyclic architectures. Additionally, they exhibit advantages such as easy preparation, convenient handling, high safety, and excellent reactivity. Consequently, CF₃- imidoyl sulfoxonium ylides have driven growing interest in their application toward synthesizing trifluoromethylfun- ctionalized heterocycles. This review systematically summarizes the recent advances in the utilization of CF₃-imidoyl sulfoxonium ylides in annulation reactions and heterocycle synthesis, while also outlining future research opportunities in this emerging field.

Key words: CF₃-imidoyl sulfoxonium ylides, annulation reactions, heterocycle compounds, trifluoromethyl

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Xiaopei Chen, Qinglong Wang, Xuehui Hou, Chuanchuan Wang, Zhiwei Ma, Jingyu Zhang. Recent Progress on the Application of CF₃-Imidoyl Sulfoxonium Ylides in Annulation Reactions[J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2796-2814.

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Fig. & Tab. 34

Scheme 1. Preparation of CF3-imidoyl sulfoxonium ylides (TFISYs)

Scheme 2. [3＋2] annulation of TFISYs with 1,3-dicarbonyl compounds

Scheme 3. [3＋2] annulation of TFISYs with α-enolic dithioesters

Scheme 4. [4＋1] annulation of TFISYs with α-halo hydrazones

Scheme 5. [3＋3] annulation of TFISYs with cyclopropenones

Scheme 6. One pot annulation of TFISYs with o-bromophenol

Scheme 7. [5＋1] annulation of TFISYs with isothiocyanates

Scheme 8. The multi-component annulation involving TFISYs

Scheme 9. [2＋2＋1] annulation of TFISYs with isothiocyanates

Scheme 10. [3＋3] annulation of TFISYs with nitrile imines

Scheme 11. [(3＋3)－1] annulation of TFISYs with pyridinium 1,4-zwitterionic thiolates

Scheme 12. [4＋2] annulation of TFISYs with acetylenic ester

Scheme 13. Stepwise [4＋2] annulation of TFISYs with 1,2-diaza-1,3-diene

Scheme 14. [5＋1] annulation of TFISYs with azo compounds

Scheme 15. [3＋2] annulation of TFISYs with alkenyl azide compounds

Scheme 16. [4＋1] annulation of TFISYs with o-methylidene quinone

Scheme 17. [4＋1] annulation of TFISYs with o-hydroxy- phenyl-p-quinone methides

Scheme 18. Insertion/annulation of TFISYs with sodium thiocyanate

Scheme 19. Substrate-regulated annulation of TFISYs with diazo compounds

Scheme 20. Visible light-induced cascade annulation of TFISYs with azide compounds

Scheme 21. Ru-catalyzed annulation of TFISYs with benzoic acids

Scheme 22. Ru-catalyzed annulation of TFISYs with α-naphthols

Scheme 23. Rh-catalyzed annulation of TFISYs with benzimidates

Scheme 24. Rh-catalyzed annulation of TFISYs with benzoylacetonitriles

Scheme 25. Rh-catalyzed annulation of TFISYs with 2-aryl-3H-indoles

Scheme 26. Rh-catalyzed asymmetric [3＋3] annulation of TFISYs with N-alkoxy benzamide

Scheme 27. Rh-catalyzed annulation of TFISYs with N-car- bamoylindoles

Scheme 28. Rh-catalyzed annulation of TFISYs with 2-aryl- oxazolines

Scheme 29. CuOTf-catalyzed annulation of TFISYs with terminal alkynes

Scheme 30. Rh-catalyzed annulation of TFISYs with 2-arylbenzimidazoles

Scheme 31. Rh-catalyzed annulation of TFISYs with 3-aryl- 1H-indazoles

Scheme 32. Rh-catalyzed annulation of TFISYs with 2-arylpyridine

Scheme 33. Rh-catalyzed annulation of TFISYs with azobenzenes

Scheme 34. Rh-catalyzed annulation of TFISYs with aryl oximes

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CF₃-亚胺酰基亚砜叶立德在环化反应中的应用研究进展

Recent Progress on the Application of CF₃-Imidoyl Sulfoxonium Ylides in Annulation Reactions

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CF3-亚胺酰基亚砜叶立德在环化反应中的应用研究进展