CF3-亚胺酰基亚砜叶立德在环化反应中的应用研究进展

doi:10.6023/cjoc202502027

有机化学 ›› 2025, Vol. 45 ›› Issue (8): 2796-2814.DOI: 10.6023/cjoc202502027 上一篇下一篇

综述与进展

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)

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摘要/Abstract

CF₃-亚胺酰基亚砜叶立德是一类重要的含三氟甲基官能团的氮杂合成子, 不仅可以作为偶极子参与串联环化反应, 还可以作为卡宾前体参与碳氢键活化/串联环化反应, 构建不同结构的含三氟甲基的环状骨架. 另外, 其具有易于制备、使用方便、安全性高、反应活性好等特点. 因此, 近年来CF₃-亚胺酰基亚砜叶立德在三氟甲基修饰的杂环化合物的合成应用中受到了极大的关注. 基于此, 系统综述了CF₃-亚胺酰基亚砜叶立德在环化反应及杂环化学中的应用, 并对该领域的研究前景进行了展望.

关键词: CF₃-亚胺酰基亚砜叶立德, 环化反应, 杂环化合物, 三氟甲基

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

引用此文

陈晓培, 王清龙, 侯学会, 王川川, 马志伟, 张京玉. CF₃-亚胺酰基亚砜叶立德在环化反应中的应用研究进展[J]. 有机化学, 2025, 45(8): 2796-2814.

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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图/表 34

图式1. CF3-亚胺酰基亚砜叶立德的制备

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

图式2. TFISYs与1,3-二羰基化合物的[3＋2]环化反应

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

图式3. TFISYs与α-烯醇化二硫酯的[3＋2]环化反应

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

图式4. TFISYs与α-卤代腙的[4＋1]环化反应

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

图式5. TFISYs与环丙烯酮的[3＋3]环化反应

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

图式6. TFISYs与邻溴苯酚的一锅法环化反应

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

图式7. TFISYs与异硫氰酸酯的[5＋1]环化反应

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

图式8. TFISYs参与的多组分环化反应

Scheme 8. The multi-component annulation involving TFISYs

图式9. TFISYs与异硫氰酸酯的[2＋2＋1]环化反应

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

图式10. TFISYs与腈亚胺的[3＋3]环化反应

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

图式11. TFISYs与1,4-吡啶硫内鎓盐的[(3＋3)－1]环化反应

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

图式12. TFISYs与炔酸酯的[4＋2]环化反应

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

图式13. TFISYs与1,2-二氮杂-1,3-二烯的分步[4＋2]环化反应

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

图式14. TFISYs与偶氮化合物的[5＋1]环化反应

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

图式15. TFISYs与烯基叠氮化合物的[3＋2]环化反应

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

图式16. TFISYs与邻甲亚基苯醌的[4＋1]环化反应

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

图式17. TFISYs与邻羟苯基甲亚基对苯醌的[4＋1]环化反应

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

图式18. TFISYs与硫氰化钠的插入环化反应

Scheme 18. Insertion/annulation of TFISYs with sodium thiocyanate

图式19. 底物调节的TFISYs与重氮化合物的环化反应

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

图式20. 可见光促进的TFISYs与叠氮化合物的串联环化反应

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

图式21. 钌催化的TFISYs与苯甲酸的环化反应

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

图式22. 钌催化的TFISYs与α-萘酚的环化反应

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

图式23. 铑催化的TFISYs与苯甲亚胺酸酯的环化反应

Scheme 23. Rh-catalyzed annulation of TFISYs with benzimidates

图式24. 铑催化的TFISYs与苯甲酰乙腈的环化反应

Scheme 24. Rh-catalyzed annulation of TFISYs with benzoylacetonitriles

图式25. 铑催化的TFISYs与2-芳基-3H-吲哚的环化反应

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

图式26. 铑催化的TFISYs与N-烷氧基苯甲酰胺的不对称[3＋3]环化反应

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

图式27. 铑催化的TFISYs与N-胺基甲酰基吲哚的环化反应

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

图式28. 铑催化的TFISYs与2-芳基噁唑啉的环化反应

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

图式29. 三氟甲磺酸铜催化的TFISYs与端炔的环化反应

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

图式30. 铑催化的TFISYs与2-芳基苯并咪唑的环化反应

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

图式31. 铑催化的TFISYs与3-芳基-1H-吲唑的环化反应

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

图式32. 铑催化的TFISYs与2-芳基吡啶的环化反应

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

图式33. 铑催化的TFISYs与偶氮苯的环化反应

Scheme 33. Rh-catalyzed annulation of TFISYs with azobenzenes

图式34. 铑催化的TFISYs与芳肟的环化反应

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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