Recent Advances in the Transformation of Difluorocyclopropenes★

doi:10.6023/A23030088

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (5): 520-532.DOI: 10.6023/A23030088 Previous Articles Next Articles

Special Issue: 庆祝《化学学报》创刊90周年合辑；有机氟化学合集

Review

二氟环丙烯参与的有机反应研究进展^★

黄家翩^a, 刘飞^a, 吴劼^*^,^a^,^b()

a 台州学院医药化工学院&高等研究院台州 318000
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

投稿日期:2023-03-21 发布日期:2023-04-20

作者简介:

黄家翩, 台州学院高等研究院实验员, 在读博士. 主要从事有机合成方法学研究. 2017年6月获得江西师范大学有机化学专业硕士学位, 随后加入中国科学院上海有机化学研究所游书力研究员课题组从事研究助理工作. 2019年8月进入台州学院工作. 至今为止, 在Nat. Commun.; ACS Catal.; Org. Lett.; Org. Chem. Front.等期刊发表SCI论文近20篇, 获得中国发明专利4项.

刘飞, 2020年6月获得南昌师范学院学士学位, 随后考入江西师范大学攻读硕士学位. 2021年7月加入台州学院吴劼教授课题组(联合培养研究生).

吴劼, 教授、博士生导师. 2000年毕业于中国科学院上海有机化学研究所获得博士学位, 2000至2004年先后在美国哈佛大学(博士后)、洛克菲勒大学艾伦·戴蒙德艾滋病研究中心(访问科学家)及VivoQuest, Inc.(研究员)从事有机合成、药物化学及相关研究工作, 2004年9月回国加入复旦大学化学系(副教授), 2006年4月晋升为教授. 2019年9月加入台州学院. 目前主要研究领域为药物结构导向的有机合成方法学研究. 独立工作以来已在Nat. Commun.; J. Am. Chem. Soc.; Angew. Chem. Int. Ed.; Chem. Soc. Rev.等国际核心期刊发表SCI论文360余篇(其中IF>5.0论文220余篇), 论文被引用18500余次, 参与编写专著四本, 独立撰写专著一本, 获得美国发明专利2项, 中国发明专利32项. 先后担任“ACS Combinatorial Science”，“化学学报”，“Applied Sciences”，“Journal of Sulfur Chemistry”等期刊编委.

^★庆祝《化学学报》创刊90周年.
谨以此文献给戴立信教授百岁生辰！

基金资助:
受国家自然科学基金(22171206); 浙江省自然科学基金(Z23B020002)

Recent Advances in the Transformation of Difluorocyclopropenes^★

Huang Jiapian^a, Liu Fei^a, Wu Jie^a^,^b()

a School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies, Taizhou University, Taizhou 318000, China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Received:2023-03-21 Published:2023-04-20
Contact: *E-mail: jie_wu@fudan.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Dedicated to Professor Li-Xin Dai on the occasion of his 100th birthday.
Supported by:
National Natural Science Foundation of China(22171206); Natural Science Foundation of Zhejiang Province(Z23B020002)

In recent years, organic reactions involving difluorocyclopropenes have attracted the attention of organic chemists and have made great progress. The reactions mainly include: (1) cyclization: a) transition-metal catalyzed C—H bond activation cyclization with directing groups; b) cyclization reactions with non-directing groups; (2) hydrogenation reduction; (3) fluorination as “F” source reagents. In this paper, the synthesis methods and applications of difluorocyclopropenes in past 10 years are summarized. The conversion reactions of difluorocyclopropenes are emphasized. Additionally, difluorocyclopropenes have aroused considerable interests both from a structural standpoint and their participation in various ring-opening reactions. Given the increasing application of cyclopropyl skeleton in the development of drugs and unarguable importance of fluorinated compounds in medicinal chemistry and agrochemistry, it is no doubt that difluorocyclopropenes are encountered into bioactive molecular and at present lie among “emerging fluorinated motifs”. Although the synthesis and application of structurally diverse difluorocyclopropenes have been witnessed in the past decade, the most widely used methods for the preparation of these compounds include difluoromethylenation of alkynes and difluoromethylation of heteroatom nucleophiles (such as NaF, NaI, ⁿBuN₄X, etc.) with a difluorocarbene reagent, which can be generated from various precursors (such as TMSCF₃, TMSCF₂X, Ph₃P^＋CF₂CO₂^-, TFDA, etc.). For the transition metal-catalyzed cyclization of difluorocyclopropenes, some common metal salts (such as rhodium, ruthenium, copper, palladium, silver) are used as catalysts. Moreover, the metallic hydrogen (M—H) reduction strategy is a simple and efficient method for the hydrogenation reduction of difluorocyclopropenes leading to difluorocyclopropanes, and the asymmetric hydrogenation reduction of difluorocyclopropenes can be achieved in the presence of chiral ligands. In fluorination reactions, difluorocyclopropenes have some advantages that cannot be achieved by traditional fluorination reagents for the direct fluorination and functionalization of hydroxyl groups (such as fluorination of polyhydroxyl alcohols). Of course, the biggest disadvantage of difluorocyclopropene as a fluorine source lies in its poor atomic economy, which has been criticized. Despite the remarkable achievements in the reactions of difluorocyclopropenes, there are still many issues that need to be addressed. For instance, difluorocyclopropenes are rarely applied in traditional radical reactions, photocatalysis, electrocatalysis and flow chemistry. Hopefully, difluorocyclopropenes can gradually appear in photo- and electro-catalyzed radical chemistry, and the related asymmetric reactions will also get more attention and development in the near future.

Key words: transition metal-catalyzed, C—H bond activation, cyclization, hydrogenation reduction, fluorination

Cite this article

Huang Jiapian, Liu Fei, Wu Jie. Recent Advances in the Transformation of Difluorocyclopropenes^★[J]. Acta Chimica Sinica, 2023, 81(5): 520-532.

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Fig. & Tab. 26

Figure 1. The synthesis of difluorocyclopropenes

Figure 2. Rhodium-catalyzed annulation reaction of N-methoxybenz- amides with difluorocyclopropenes

Figure 3. Possible mechanism

Figure 4. Rh-catalyzed three-component reactions of heteroarenes, difluorocyclopropenes and water

Figure 5. Ru-catalyzed three-component reactions of 2-phenylquinazo- linones, difluorocyclopropenes and water and possible mechanism

Figure 6. Rh-catalyzed annulation of 1-arylpyrazolidinones with difluorocyclopropenes giving fluorinated pyridopyrimidinone derivatives

Figure 7. Rh-catalyzed annulation cascade of N-sulfonyl-2-aminobenz- aldehydes with difluorocyclopropenes

Figure 8. Rh-catalyzed [3＋2] annulation reactions of difluorocyclopropenes with alkynes

Figure 9. Cu- or Ag-catalyzed [3＋2] annulation reactions of difluorocyclopropenes with N,N-dialkylformamides and difluorocyclopropene itself

Figure 10. Photo-/Pd-catalyzed [3＋2] annulation reactions of difluorocyclopropenes with olefins

Figure 11. Metal free-catalyzed three component reactions of difluorocyclopropenes, (benzo) pyridines and tetrazines

Figure 12. Metal-free-catalyzed three component reactions of difluorocyclopropenes, (benzo) pyridines and nucleophilic reagents

Figure 13. Cu-catalyzed [3＋3] cycloaddition reactions of difluorocyclopropenes and methylene isocyanides

Figure 14. Ag-catalyzed [3＋3] cycloaddition reactions of difluorocyclopropenes and isocyanides

Figure 15. Base-catalyzed [3＋3] cycloaddition reactions of difluorocyclopropenes and diazo compounds

Figure 16. Photo-catalyzed [2＋3] cycloaddition reactions of difluorocyclopropenes and cyclopropylanilines

Figure 17. Pd-catalyzed [2＋4] cycloaddition reactions of difluorocyclopropenes and silacyclobutanes (SCBs)

Figure 18. Selected examples of bioactive difluorocyclopropanes

Figure 19. One-pot synthesis of chiral cyclopropane compounds

Figure 20. Ru-catalyzed asymmetric hydrogenation of difluorocyclopropenes

Figure 21. Cu-catalyzed asymmetric hydrogenation of difluorocyclopropenes

Figure 22. Cu-catalyzed hydroborylation and hydrosilylation of difluorocyclopropenes with B2pin2 and PhMe2Si-Bpin

Figure 23. Cu-catalyzed asymmetric hydrosilylation of difluorocyclopropenes with PhMe2Si-Bpin

Figure 24. Photo-/Pd-catalyzed hydroalkenylation reactions of difluorocyclopropenes with olefins

Figure 25. Deoxyfluorination of alcohols using difluorocyclopropenes as fluorine sources

Figure 26. Acyl-fluorination of carboxylic acids using difluorocyclopropenes as fluorine sources

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二氟环丙烯参与的有机反应研究进展^★

Recent Advances in the Transformation of Difluorocyclopropenes^★

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二氟环丙烯参与的有机反应研究进展★

Recent Advances in the Transformation of Difluorocyclopropenes★

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Fig. & Tab. 26

References 56

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二氟环丙烯参与的有机反应研究进展^★

Recent Advances in the Transformation of Difluorocyclopropenes^★