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

doi:10.6023/cjoc202305012

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (12): 4036-4056.DOI: 10.6023/cjoc202305012 Previous Articles Next Articles

REVIEWS

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)

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

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 30

Figure 1. Organic phosphine-promoted deoxygenative functionalization

Scheme 1. Deoxyalkylation of aromatic carboxylic acids

Scheme 2. Deoxygenative protonation of carboxylic acids

Scheme 3. Deoxyalkylation of carboxylic acids

Scheme 4. Deoxygenative deuterization of carboxylic acids

Scheme 5. Deoxyarylation of aromatic carboxylic acids

Scheme 6. Deoxygenative esterification of carboxylic acids

Scheme 7. Intermolecular deoxygenative cyclization of aromatic carboxylic acids

Scheme 8. Deoxygenative functionalization of aromatic carboxylic acids

Scheme 9. Deoxygenative acylation of carboxylic acids

Scheme 10. Carboxylic acid deoxyamidation

Scheme 11. Deoxydifluoroallylation of carboxylic acids

Scheme 12. Deoxyalkylation for β-ketogem diboronenes

Scheme 13. Deoxygenative spirocylation of Aromatic carboxylic acids

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

Scheme 15. Deoxygenative aminoalkylation of alcohols

Scheme 16. Alcohol deoxygenation Giese reaction

Scheme 17. Deoxygenative alkenylation of alcohols

Scheme 18. Alcohol deoxidation ammonia alkylation

Scheme 19. Deoxygenative difluoroethylation of alcohols

Scheme 20. Alcohol/thiol deoxygenation/thiopyridinization

Scheme 21. Deoxypolyfluoroalkylation

Scheme 22. Deoxyalkylation of xanthate

Scheme 23. Deoxyhydroamination of terminal alkenes

Scheme 24. Deoxyhydroamination of N-hydroxyphthalimide with alkenes

Scheme 25. Deoxyarylation of N-hydroxyphthalimide

Scheme 26. Synthesis of aniline by deoxidation

Scheme 27. Cycloketoxime deoxyalkylation and difluoroenylation

Scheme 28. N-Hydroxyamides deoxyphosphorylation

Scheme 29. Synthesis of sulfide via deoxyfunctionalization

References 48

[1]	(a) Westheimer F. H. Science 1987, 235, 1173. pmid: 2434996
	(b) Petkowski J. J.; Bains W.; Seager S. Molecules 2019, 24, 866. doi: 10.3390/molecules24050866 pmid: 2434996
[2]	(a) Ardito F.; Giuliani M.; Perrone D.; Troiano G.; Lo Muzio L. Int. J. Mol. Med. 2017, 40, 271. doi: 10.3892/ijmm.2017.3036
	(b) Sun Z.; Xiao L.; Chen Y.; Wang J.; Zeng F.; Zhang H.; Zhang J.; Yang K.; Hu Y. J. ACS Med. Chem. Lett. 2023, 14, 473. doi: 10.1021/acsmedchemlett.3c00022
[3]	Clearfield A.; Demadis K. D. Metal Phosphonate Chemistry: From Synthesis to Applications, The Royal Society of Chemistry, 2011, pp. 223-227.
[4]	(a) Wang T.; Han X.; Zhong F.; Yao W.; Lu Y. Acc. Chem. Res. 2016, 49, 1369. doi: 10.1021/acs.accounts.6b00163 pmid: 32491839
	(b) Ni H.; Chan W.-L.; Lu Y. Chem. Rev. 2018, 118, 9344. doi: 10.1021/acs.chemrev.8b00261 pmid: 32491839
	(c) Clevenger A. L.; Stolley R. M.; Aderibigbe J.; Louie J. Chem. Rev. 2020, 120, 6124. doi: 10.1021/acs.chemrev.9b00682 pmid: 32491839
[5]	(a) Wang M.; Wang C.; Huo Y.; Dang X.; Xue H.; Liu L.; Chai H.; Xie X.; Li Z.; Lu D.; Xu Z. Nat. Commun. 2021, 12, 6873. doi: 10.1038/s41467-021-27086-x
	(b) Lubaev A. E.; Rathnayake M. D.; Eze F.; Bayeh-Romero L. J. Am. Chem. Soc. 2022, 144, 13294. doi: 10.1021/jacs.2c04588
[6]	Zhang X.; Yuan Q.; Zhang H.; Shen Z.-J.; Zhao L.; Yang C.; Guo L.; Xia W. Green. Chem. 2023, 25, 1435. doi: 10.1039/D2GC04559A
[7]	Shao X.; Zheng Y.; Ramadoss V.; Tian L.; Wang Y. Org. Biomol. Chem. 2020, 18, 5994. doi: 10.1039/D0OB01083A
[8]	Ye Z.-P.; Hu Y.-Z.; Xia P.-J.; Xiang H.-Y.; Chen K.; Yang H. Org. Chem. Front. 2021, 8, 273. doi: 10.1039/D0QO01321H
[9]	Hu X.-Q.; Hou Y.-X.; Liu Z.-K.; Gao Y. Org. Chem. Front. 2020, 7, 2319. doi: 10.1039/D0QO00643B
[10]	Zhang M.; Xie J.; Zhu C. Nat. Commun. 2018, 9, 3517. doi: 10.1038/s41467-018-06019-1
[11]	Stache E. E.; Ertel A. B.; Rovis T.; Doyle A. G. ACS Catal. 2018, 8, 11134. doi: 10.1021/acscatal.8b03592 pmid: 31367474
[12]	Martinez Alvarado J. I.; Ertel A. B.; Stegner A.; Stache E. E.; Doyle A. G. Org. Lett. 2019, 21, 9940. doi: 10.1021/acs.orglett.9b03871 pmid: 31750667
[13]	Zhang M.; Yuan X.-A.; Zhu C.; Xie J. Angew. Chem., Int. Ed. 2019, 58, 312. doi: 10.1002/anie.v58.1
[14]	Ruzi R.; Ma J.; Yuan X.-A.; Wang W.; Wang S.; Zhang M.; Dai J.; Xie J.; Zhu C. Chem.-Eur. J. 2019, 25, 12724. doi: 10.1002/chem.v25.55
[15]	März M.; Kohout M.; Neveselý T.; Chudoba J.; Prukała D.; Niziński S.; Sikorski M.; Burdziński G.; Cibulka R. Org. Biomol. Chem. 2018, 16, 6809. doi: 10.1039/C8OB01822G
[16]	Jiang H.; Mao G.; Wu H.; An Q.; Zuo M.; Guo W.; Xu C.; Sun Z.; Chu W. Green Chem. 2019, 21, 5368. doi: 10.1039/C9GC02380A
[17]	Ruzi R.; Liu K.; Zhu C.; Xie J. Nat. Commun. 2020, 11, 3312. doi: 10.1038/s41467-020-17224-2
[18]	Zhang L.; Chen S.; He H.; Li W.; Zhu C.; Xie J. Chem. Commun. 2021, 57, 9064. doi: 10.1039/D1CC04188F
[19]	Ning Y.; Wang S.; Li M.; Han J.; Zhu C.; Xie J. Nat. Commun. 2021, 12, 4637. doi: 10.1038/s41467-021-24908-w
[20]	Guo Y.-Q.; Wang R.; Song H.; Liu Y.; Wang Q. Org. Lett. 2020, 22, 709. doi: 10.1021/acs.orglett.9b04504
[21]	Nagaraju A.; Saiaede T.; Eghbarieh N.; Masarwa A. Chem.-Eur. J. 2023, 29, e202202646. doi: 10.1002/chem.v29.3
[22]	Yang W.-C.; Zhang M.-M.; Feng J.-G. Adv. Synth. Catal. 2020, 362, 4446. doi: 10.1002/adsc.v362.21
[23]	Zhou C.; Shatskiy A.; Temerdashev A. Z.; Kärkäs M. D.; Dinér P. Commun. Chem. 2022, 5, 92. doi: 10.1038/s42004-022-00706-3
[24]	Han J.-B.; Guo A.; Tang X.-Y. Chem.-Eur. J. 2019, 25, 2989. doi: 10.1002/chem.v25.12
[25]	de Pedro Beato E.; Mazzarella D.; Balletti M.; Melchiorre P. Chem. Sci. 2020, 11, 6312. doi: 10.1039/D0SC02313B
[26]	Nanjo T.; Matsugasako T.; Maruo Y.; Takemoto Y. Org. Lett. 2022, 24, 359. doi: 10.1021/acs.orglett.1c04029
[27]	Guo H. M.; Wu X. Nat. Commun. 2021, 12, 5365. doi: 10.1038/s41467-021-25702-4
[28]	Guo H.-M.; He B.-Q.; Wu X. Org. Lett. 2022, 24, 3199. doi: 10.1021/acs.orglett.2c00889
[29]	Zhang W.; Ning S.; Li Y.; Wu X. Chem. Commun. 2022, 58, 12843. doi: 10.1039/D2CC05098F
[30]	Xia G.-D.; He Y.-Y.; Zhang J.; Liu Z.-K.; Gao Y.; Hu X.-Q. Chem. Commun. 2022, 58, 6733. doi: 10.1039/D2CC01918C
[31]	Tan C.-Y.; Kim M.; Park I.; Kim Y.; Hong S. Angew. Chem., Int. Ed. 2022, 61, e202213857. doi: 10.1002/anie.v61.51
[32]	Xie Z.-Z.; Zheng Y.; Yuan C.-P.; Guan J.-P.; Ye Z.-P.; Xiao J.-A.; Xiang H.-Y.; Chen K.; Chen X.-Q.; Yang H. Angew. Chem., Int. Ed. 2022, 61, e202211035. doi: 10.1002/anie.v61.45
[33]	Chheda P. R.; Simmons N.; Schuman D. P.; Shi Z. Org. Lett. 2022, 24, 9514. doi: 10.1021/acs.orglett.2c03994
[34]	(a) Zou D.; Wang W.; Hu Y.; Jia T. Org. Biomol. Chem. 2023, 21, 2254. doi: 10.1039/D3OB00064H
	(b) Cui S.; Zeng L. Nat. Chem. 2023, 15, 597. doi: 10.1038/s41557-023-01182-5
[35]	Xu Z.; Feng J.; Yao P.; Wu Q.; Zhu D. Green Chem. 2023, 25, 4667. doi: 10.1039/D3GC00047H
[36]	Ouyang L.; Miao R.; Yang Z.; Luo R. J. Catal. 2023, 418, 283. doi: 10.1016/j.jcat.2023.01.030
[37]	(a) Irrgang T.; Kempe R. Chem. Rev. 2020, 120, 9583. doi: 10.1021/acs.chemrev.0c00248
	(b) Das K.; Sarkar K.; Maji B. ACS Catal. 2021, 11, 7060. doi: 10.1021/acscatal.1c01199
[38]	Lardy S. W.; Schmidt V. A. J. Am. Chem. Soc. 2018, 140, 12318. doi: 10.1021/jacs.8b06881
[39]	Pan Z.; Chen B.; Fang J.; Liu T.; Fang J.; Ma Y. J. Org. Chem. 2022, 87, 14588. doi: 10.1021/acs.joc.2c01975
[40]	Lardy S. W.; Luong K. C.; Schmidt V. A. Chem.-Eur. J. 2019, 25, 15267. doi: 10.1002/chem.v25.67
[41]	Xia P.-J.; Ye Z.-P.; Hu Y.-Z.; Song D.; Xiang H.-Y.; Chen X.-Q.; Yang H. Org. Lett. 2019, 21, 2658. doi: 10.1021/acs.orglett.9b00651
[42]	Han W.; Su J.; Mo J.-N.; Zhao J. Org. Lett. 2022, 24, 6247. doi: 10.1021/acs.orglett.2c02226
[43]	Carreno M. C. Chem. Rev. 1995, 95, 1717. doi: 10.1021/cr00038a002
[44]	Surur A. S.; Schulig L.; Link A. Arch. Pharm. 2019, 352, 1800248.
[45]	García N.; García-García P.; Fernández-Rodríguez M. A.; García D.; Pedrosa M. R.; Arnáiz F. J.; Sanz R. Green Chem. 2013, 15, 999. doi: 10.1039/c3gc36908k
[46]	Zhang J.; Gao X.; Zhang C.; Zhang C.; Luan J.; Zhao D. Synth. Commun. 2010, 40, 1794. doi: 10.1080/00397910903161819
[47]	(a) Iranpoor N.; Firouzabadi H.; Shaterian H. R. J. Org. Chem. 2002, 67, 2826. pmid: 29381151
	(b) Jang Y.; Kim K. T.; Jeon H. B. J. Org. Chem. 2013, 78, 6328. doi: 10.1021/jo4008157 pmid: 29381151
	(c) Zhao X.; Zheng X.; Yang B.; Sheng J.; Lu K. Org. Biomol. Chem. 2018, 16, 1200. doi: 10.1039/c7ob02834b pmid: 29381151
[48]	Clarke A. K.; Parkin A.; Taylor R. J. K.; Unsworth W. P.; Rossi-Ashton J. A. ACS Catal. 2020, 10, 5814. doi: 10.1021/acscatal.0c00690 pmid: 32582464

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

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 30

References 48

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yatong Fu, Chaofan Sun, Dan Zhang, Chengguo Jin, Juyou Lu. Recent Progress in B—H Bond Functionalization of nido-Carboranes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 438-447.
[2]	Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348.
[3]	Yanshuo Zhu, Hongyan Wang, Penghua Shu, Ke'na Zhang, Qilin Wang. Recent Advances on Alkoxy Radicals-Mediated C(sp³)—H Bond Functionalization via 1,5-Hydrogen Atom Transfer [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 1-17.
[4]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[5]	Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.
[6]	Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136.
[7]	Sijie Fan, Wuheng Dong, Caiyun Liang, Guichao Wang, Yao Yuan, Zuodong Yin, Zhaoguo Zhang. Visible Light-Induced Radical Cyclization for the Construction of 4-Aryl-1,2-dihydronaphthalenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3277-3286.
[8]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[9]	Yingjie Liu, Gangqing Shi, Ge Chou, Xin Zhang, Dongxue Song, Ning Chen, Miao Yu, Ying Xu. Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2664-2681.
[10]	Min Wu, Bo Liu, Jialong Yuan, Qiang Fu, Rui Wang, Dawei Lou, Fushun Liang. Recent Progress in the C—S Bond Formation Reactions Mediated by Visible Light [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2269-2292.
[11]	Xiaoping Xu, Yifei Zhang, Xiaoyu Mo, Jun Jiang. Rh-Catalyzed C—H Functionalization Reaction between 3-Diazoindolin-2-imines and Pyrazolones for the Construction of 3-Pyrazolyl Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2519-2527.
[12]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[13]	Jiamin Ma, Jiaoxiong Li, Qiansen Meng, Xianghua Zeng. Advances on the Radical Sulfonation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2040-2052.
[14]	Rongbin Cai, Bing Li, Qi Zhou, Longyi Zhu, Jun Luo. Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2217-2225.
[15]	Linsheng Bai, Peng Hong, Anguo Ying. Research Progress of Functional Polyacrylonitrile Fiber in Promoting Organic Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1241-1270.