可见光诱导有机膦促进脱氧官能化反应研究进展

doi:10.6023/cjoc202305012

有机化学 ›› 2023, Vol. 43 ›› Issue (12): 4036-4056.DOI: 10.6023/cjoc202305012 上一篇下一篇

综述与进展

可见光诱导有机膦促进脱氧官能化反应研究进展

汤娟^a^,^b, 胡家榆^c, 祝志强^c^,^*(), 蒲守智^a^,^*()

a 江西科技师范大学江西省有机功能分子重点实验室南昌 330038
b 江西师范大学江西省绿色化学重点实验室南昌 330022
c 东华理工大学江西省合成化学重点实验室南昌 330013

收稿日期:2023-05-11 修回日期:2023-07-06 发布日期:2023-08-30
基金资助:
国家自然科学基金(21864013); 国家自然科学基金(22263005); 江西省自然科学基金(20212BCJL23057); 江西省自然科学基金(20224ACB203006); 江西省自然科学基金(20232BAB203001); 江西省博士后基金(2019KY40)

Recent Advances in Visible-Light-Induced Organic Phosphine- Promoted Deoxygenative Functionalization Reactions

Juan Tang^a^,^b, Jiayu Hu^c, Zhiqiang Zhu^c,*(), Shouzhi Pu^a,*()

a Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013
b Key Laboratory for Green Chemistry of Jiangxi Province, Jiangxi Normal University, Nanchang 330022
c Jiangxi Province Key Laboratory of Synthetic Chemistry, East China University of Technology, Nanchang 330013

Received:2023-05-11 Revised:2023-07-06 Published:2023-08-30
Contact: *E-mail: pushouzhi@tsinghua.org.cn;zhuzq@ecut.edu.cn
Supported by:
National Natural Science Foundation of China(21864013); National Natural Science Foundation of China(22263005); Natural Science Foundation of Jiangxi Province(20212BCJL23057); Natural Science Foundation of Jiangxi Province(20224ACB203006); Natural Science Foundation of Jiangxi Province(20232BAB203001); Postdoctoral Foundation of Jiangxi Province(2019KY40)

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摘要/Abstract

脱氧偶联反应是有机化学中的重要合成转化, 有机膦促进的有机合成反应近年来发展迅速, 三苯基膦及其衍生物是有机膦中重要的一类, 其在有机合成反应中不仅可以作为配体, 而且可以用作脱氧促进剂. 最近几年, 可见光诱导有机膦促进脱氧偶联反应受到研究者们广泛关注, 该类型反应利用有机膦在可见光下经单电子转移后与含氧有机分子形成P—O中间体, 随后经脱氧得到高活性自由基物种, 并最终完成脱氧偶联, 反应底物无需预先官能团化且条件温和. 系统地概述了近年来光氧化还原诱导下有机膦促进含氧有机分子脱氧官能化反应的研究进展.

关键词: 可见光, 有机膦, 脱氧, 自由基, 官能化

Organic phosphine-promoted organic synthesis reactions have developed rapidly in recent years. Triphenylphos- phine and their derivatives are the most important class of organic phosphine compounds, which can not only serve as ligands in organic synthesis reactions, but also serve as deoxygenative promoters in a large number of reactions. In recent years, visible-light-induced deoxygenative coupling reactions have aroused considerable attention. This type of reaction uses organic phosphines to promote single electron transfer to form P—O intermediates with oxygen-containing organic molecules under visible-light, followed by deoxidation to obtain highly active free radical species, and then deoxygenative coupling to afford the desired products. Herein, the recent research progress in photoredox-induced organic phosphine-promoted deoxygenative functionalization reactions is summarized.

Key words: visible-light, organic phosphine, deoxygenation, free radical, functionalization

引用此文

汤娟, 胡家榆, 祝志强, 蒲守智. 可见光诱导有机膦促进脱氧官能化反应研究进展[J]. 有机化学, 2023, 43(12): 4036-4056.

Juan Tang, Jiayu Hu, Zhiqiang Zhu, Shouzhi Pu. Recent Advances in Visible-Light-Induced Organic Phosphine- Promoted Deoxygenative Functionalization Reactions[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4036-4056.

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图/表 30

图1. 有机膦促进脱氧官能化

Figure 1. Organic phosphine-promoted deoxygenative functionalization

图式1. 芳香族羧酸脱氧烷基化

Scheme 1. Deoxyalkylation of aromatic carboxylic acids

图式2. 羧酸脱氧质子化

Scheme 2. Deoxygenative protonation of carboxylic acids

图式3. 羧酸脱氧烷基化

Scheme 3. Deoxyalkylation of carboxylic acids

图式4. 羧酸脱氧氘化

Scheme 4. Deoxygenative deuterization of carboxylic acids

图式5. 芳香族羧酸脱氧芳基化

Scheme 5. Deoxyarylation of aromatic carboxylic acids

图式6. 羧酸脱氧酯化

Scheme 6. Deoxygenative esterification of carboxylic acids

图式7. 芳香族羧酸脱氧分子内环化

Scheme 7. Intermolecular deoxygenative cyclization of aromatic carboxylic acids

图式8. 芳香族羧酸脱氧官能化

Scheme 8. Deoxygenative functionalization of aromatic carboxylic acids

图式9. 芳香族羧酸脱氧酰基化

Scheme 9. Deoxygenative acylation of carboxylic acids

图式10. 羧酸脱氧酰胺化

Scheme 10. Carboxylic acid deoxyamidation

图式11. 芳香族羧酸脱氧二氟烯丙基化

Scheme 11. Deoxydifluoroallylation of carboxylic acids

图式12. 脱氧烷基化合成β-酮宝石二硼烯

Scheme 12. Deoxyalkylation for β-ketogem diboronenes

图式13. 芳香族羧酸脱氧串联螺环化

Scheme 13. Deoxygenative spirocylation of Aromatic carboxylic acids

图式14. N-烷氧基邻苯二甲酰亚胺脱氧官能化

Scheme 14. Deoxyfunctionalization of N-alkoxy-o-phthalimides

图式15. 醇脱氧氨烷基化

Scheme 15. Deoxygenative aminoalkylation of alcohols

图式16. 醇脱氧Giese反应

Scheme 16. Alcohol deoxygenation Giese reaction

图式17. 醇脱氧烯基化

Scheme 17. Deoxygenative alkenylation of alcohols

图式18. 醇脱氧氨烷基化

Scheme 18. Alcohol deoxidation ammonia alkylation

图式19. 醇脱氧二氟乙烯化

Scheme 19. Deoxygenative difluoroethylation of alcohols

图式20. 醇/硫醇脱氧/硫吡啶化

Scheme 20. Alcohol/thiol deoxygenation/thiopyridinization

图式21. 脱氧多氟烷基化

Scheme 21. Deoxypolyfluoroalkylation

图式22. 黄原酸盐脱氧烷基化

Scheme 22. Deoxyalkylation of xanthate

图式23. 末端烯烃脱氧氢胺化

Scheme 23. Deoxyhydroamination of terminal alkenes

图式24. N-羟基邻苯二甲酰亚胺与烯烃脱氧氢胺化

Scheme 24. Deoxyhydroamination of N-hydroxyphthalimide with alkenes

图式25. N-羟基邻苯二甲酰亚胺脱氧芳基化

Scheme 25. Deoxyarylation of N-hydroxyphthalimide

图式26. 羟肟酸脱氧合成苯胺

Scheme 26. Synthesis of aniline by deoxidation

图式27. 环酮肟脱氧烷基化和二氟烯基化

Scheme 27. Cycloketoxime deoxyalkylation and difluoroenylation

图式28. N-羟基酰胺脱氧磷酰化

Scheme 28. N-Hydroxyamides deoxyphosphorylation

图式29. 亚砜脱氧合成硫醚

Scheme 29. Synthesis of sulfide via deoxyfunctionalization

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可见光诱导有机膦促进脱氧官能化反应研究进展

Recent Advances in Visible-Light-Induced Organic Phosphine- Promoted Deoxygenative Functionalization Reactions

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