Recent Advances in Ionic Transfer Reactions

doi:10.6023/cjoc202211047

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (3): 1036-1044.DOI: 10.6023/cjoc202211047 Previous Articles Next Articles

Special Issue: 中国女科学家专辑

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离子转移反应的研究进展

李落墨, 杨小会^*()

北京理工大学前沿交叉科学研究院&化学与化工学院医药分子科学与制剂工程工信部重点实验室北京 100081

收稿日期:2022-11-30 修回日期:2023-01-05 发布日期:2023-01-11
通讯作者: 杨小会
基金资助:
国家自然科学基金(22201018); 北京市自然科学基金(2222024); 国家重点研发计划(2021YFA1401200)

Recent Advances in Ionic Transfer Reactions

Luomo Li, Xiaohui Yang()

Key Laboratory of Medical Molecule Science and Pharmaceutics Engineering, Ministry of Industry and Information Technology, Advanced Research Institute of Multidisciplinary Science & School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081

Received:2022-11-30 Revised:2023-01-05 Published:2023-01-11
Contact: Xiaohui Yang
Supported by:
National Natural Science Foundation of China(22201018); Beijing Natural Science Foundation(2222024); National Key Research and Development Program of China(2021YFA1401200)

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Abstract

In recent years, a series of novel organic reactions, named “ionic transfer reaction”, has received much attention. This kind of reaction has a characteristic mechanism and avoids the use of inflammable, explosive, highly toxic and other difficult to operate reagents. It provides a new powerful tool for transfer functionalizations of unsaturated compounds, such as transfer hydrosilylations, transfer hydrogenations, transfer hydrohalogenations, and transfer hydrocyanations. Herein, the recent progress of ionic transfer reactions and related mechanisms are summarized. Furthermore, the future developments of ionic transfer reactions are prospected.

Key words: ionic transfer reaction, transfer hydrofunctionalization, olefins, addition reaction, catalysis

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Luomo Li, Xiaohui Yang. Recent Advances in Ionic Transfer Reactions[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1036-1044.

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Fig. & Tab. 21

Scheme 1. Mechanism of ionic transfer reaction

Scheme 2. Elimination of the silane from the N-silyl-dihydro- pyridine

Scheme 3. Reaction mechanism of B(C6F5)3-catalyzed in situ silane generation

Scheme 4. B(C6F5)3-catalyzed transfer hydrosilylation of alkenes

Scheme 5. Transfer hydrosilylation of alkenes utilizing the SiH4-surrogates

Scheme 6. Hydride abstraction from amino methylene

Scheme 7. Transfer hydrogenation utilizing diisopropylamine as the hydrogen donor

Scheme 8. Transfer hydrogenation of imines utilizing 1,4-cyclo- hexadiene-type hydrogen donor

Scheme 9. Transfer hydrogenation of alkenes utilizing 1,4- cyclohexadiene-type hydrogen donor

Scheme 10. Br?nsted acid-catalyzed transfer hydrogenation of alkenes and imines

Scheme 11. InBr3-catalyzed reductive cyclization of 2-alkynyl enones

Scheme 12. Regioselectivities of ionic transfer hydrodeuteration reactions

Scheme 13. B(C6F5)3-catalyzed regioselective ionic transfer hydrodeuteration of alkenes

Scheme 14. BF3-catalyzed regiodivergent ionic transfer hydrodeuteration of alkenes

Scheme 15. InBr3-catalyzed regiodivergent ionic transfer hydro- deuteration of alkenes

Scheme 16. Br?nsted acid-catalyzed ionic transfer hydroiodination of alkynes

Scheme 17. Br?nsted acid-catalyzed ionic transfer hydrobromination of alkynes

Scheme 18. Br?nsted acid-catalyzed ionic transfer hydrochlorination reaction

Scheme 19. Ionic transfer hydrogermylation reaction

Scheme 20. Ionic transfer hydrocyanation reaction

Scheme 21. Ionic transfer hydromethallylation reaction

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离子转移反应的研究进展

Recent Advances in Ionic Transfer Reactions

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Fig. & Tab. 21

References 29

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