Photoinduced Decarboxylative Amination Driven by Electron Donor-Acceptor Complex

doi:10.6023/cjoc202407010

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (5): 1747-1754.DOI: 10.6023/cjoc202407010 Previous Articles Next Articles

ARTICLES

光诱导电子供体-受体复合物驱动的脱羧胺化

高昂^a, 闫陆宇^a, 王光祖^b, 付明臣^a^,^*()

^a 合肥工业大学化学与化工学院合肥 230009
^b 安徽科芯微流化工科技有限公司合肥 230061

收稿日期:2024-07-04 修回日期:2024-08-02 发布日期:2024-09-26
基金资助:
国家自然科学基金(22101272); 中央高校基本科研业务费(JZ2023YQTD0074)

Photoinduced Decarboxylative Amination Driven by Electron Donor-Acceptor Complex

Ang Gao^a, Luyu Yan^a, Guangzu Wang^b, Mingchen Fu^a^,^*()

^a School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009
^b Anhui Kexin Microflow Chemical Technology Co. LTD, Hefei 230061

Received:2024-07-04 Revised:2024-08-02 Published:2024-09-26
Contact: * E-mail: mcfu@hfut.edu.cn
Supported by:
National Natural Science Foundation of China(22101272); Fundamental Research Funds for the Central Universities(JZ2023YQTD0074)

1. .pdf(1447KB)

Abstract

A facile method for decarboxylative amination driven by the photoactivity of electron donor-acceptor (EDA) complexes assembled from iodide salts and redox-active esters has been proposed. A broad array of acyclic and cyclic protected amines were readily synthesized without requiring exogenous transition-metal or photoredox catalysts. Moreover, this approach facilitates late-stage functionalization of complex molecules and is amenable to continuous-flow process on gram scale.

Key words: photoredox, decarboxylative amination, iodine anion, electron donor-acceptor complex

Cite this article

Ang Gao, Luyu Yan, Guangzu Wang, Mingchen Fu. Photoinduced Decarboxylative Amination Driven by Electron Donor-Acceptor Complex[J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1747-1754.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 17

[1]	(a) Gallezot P. Chem. Soc. Rev. 2012, 41, 153.
	(b) Gooßen L. J.; Rodríguez N.; Gooßen K. Angew. Chem., Int. Ed. 2008, 47, 3100.
[2]	(a) Rodríguez N.; Goossen L. J. Chem. Soc. Rev. 2011, 40, 5030. doi: 10.1039/c1cs15093f pmid: 21792454
	(b) Xuan J.; Zhang Z.-G.; Xiao W.-J. Angew. Chem., Int. Ed. 2015, 54, 15632. pmid: 21792454
	(c) Schwarz J.; König B. Green Chem. 2018, 20, 323. pmid: 21792454
[3]	(a) Kochi J. K. J. Am. Chem. Soc. 1965, 87, 2500.
	(b) Yin F.; Wang Z.; Li Z.; Li C. J. Am. Chem. Soc. 2012, 134, 10401.
	(c) Fu M.-C.; Wang J.-X.; Shang R. Org. Lett. 2020, 22, 8572.
	(d) Wu J.; Shu C.; Li Z.; Noble A.; Aggarwal V. K. Angew. Chem., Int. Ed. 2023, 62, e202309684.
[4]	Parida S. K.; Mandal T.; Das S.; Hota S. K.; De Sarkar S.; Murarka S. ACS Catal. 2021, 11, 1640.
[5]	(a) Fawcett A.; Pradeilles J.; Wang Y.; Mutsuga T.; Myers E. L.; Aggarwal V. K. Science 2017, 357, 283.
	(b) Li C.; Wang J.; Barton L. M.; Yu S.; Tian M.; Peters D. S.; Kumar M.; Yu A. W.; Johnson K. A.; Chatterjee A. K.; Yan M.; Baran P. S. Science 2017, 356, eaam7355.
[6]	Zhou M.-D.; Qin P.; Jing L.; Sun J.; Du H.-W. Chin. J. Org. Chem. 2020, 40, 598 (in Chinese).
	(周明东, 覃丕涛, 经理珂, 孙京, 杜海武, 有机化学, 2020, 40, 598.) doi: 10.6023/cjoc201909030
[7]	Talekar S. S.; Dutta S.; Mane M. V.; Maity B. Eur. J. Org. Chem. 2024, 27, e202301312.
[8]	Zhao W.; Wurz R. P.; Peters J. C.; Fu G. C. J. Am. Chem. Soc. 2017, 139, 12153. doi: 10.1021/jacs.7b07546 pmid: 28841018
[9]	Mao R.; Balon J.; Hu X. Angew. Chem., Int. Ed. 2018, 57, 9501.
[10]	Chandrachud P. P.; Wojtas L.; Lopchuk J. M. J. Am. Chem. Soc. 2020, 142, 21743. doi: 10.1021/jacs.0c09403 pmid: 33332115
[11]	Cai Y.-M.; Liu X.-T.; Xu L.-L.; Shang M. Angew. Chem., Int. Ed. 2024, 63, e202315222.
[12]	(a) Yan T.; Yang J.; Yan K.; Wang Z.; Li B.; Wen J. Angew. Chem., Int. Ed. 2024, e202405186. pmid: 32134647
	(b) Crisenza G. E. M.; Mazzarella D.; Melchiorre P. J. Am. Chem. Soc. 2020, 142, 5461-5476. doi: 10.1021/jacs.0c01416 pmid: 32134647
[13]	Fu M.-C.; Shang R.; Zhao B.; Wang B.; Fu Y. Science 2019, 363, 1429.
[14]	(a) Wang J.-X.; Fu M.-C.; Yan L.-Y.; Lu X.; Fu Y. Adv. Sci. 2024, 11, 2307241.
	(b) Wang J.-X.; Wang Y.-T.; Zhang H.; Fu M.-C. Org. Chem. Front. 2021, 8, 4466.
	(c) Wang G.-Z.; Fu M.-C.; Zhao B.; Shang R. Sci. China Chem. 2021, 64, 43.
[15]	(a) Zhao H.; Xi X.; Wu T.; Chen Z.; Wang M.; Yuan W. Sci. China Chem. 2024, 67, 3019.
	(b) Li B.; Yi L.; Maity B.; Jia J.; Shen Y.; Chen X.-Y.; Cavallo L.; Rueping M. ACS Catal. 2023, 13, 15194.
	(c) Chen F.; Bai M.; Zhang Y.; Liu W.; Huangfu X.; Liu Y.; Tang G.; Zhao Y. Angew. Chem., Int. Ed. 2022, 61, e202210334.
	(d) Li R.-H.; Zhao Y.-L.; Shang Q.-K.; Geng Y.; Wang X.-L.; Su Z.-M.; Li G.-F.; Guan W. ACS Catal. 2021, 11, 6633.
	(e) Liu H.-Y.; Lu Y.; Li Y.; Li J.-H. Org. Lett. 2020, 22, 8819.
[16]	Peacock D. M.; Roos C. B.; Hartwig J. F. ACS Cent. Sci. 2016, 2, 647.
[17]	Tucker J. W.; Zhang Y.; Jamison T. F.; Stephenson C. R. J. Angew. Chem., Int. Ed. 2012, 51, 4144.

Entry	Variations from the above conditions	Yield^a/%
1	None	70
2	5 mol% TBAI	73
3	30 mol% TBAI	61
4	DMF instead of DMA	63
5	NMP instead of DMA	50
6	Acetone instead of DMA	14
7	LiI, NaI, or KI instead of TBAI	33~61
8	1b instead of 1a	30
9	1c instead of 1a	28
10	1d instead of 1a	37
11	No light (50 ℃) or TBAI	0

Entry	Variations from the above conditions	Yield^a/%
1	None	70
2	5 mol% TBAI	73
3	30 mol% TBAI	61
4	DMF instead of DMA	63
5	NMP instead of DMA	50
6	Acetone instead of DMA	14
7	LiI, NaI, or KI instead of TBAI	33~61
8	1b instead of 1a	30
9	1c instead of 1a	28
10	1d instead of 1a	37
11	No light (50 ℃) or TBAI	0

光诱导电子供体-受体复合物驱动的脱羧胺化

Photoinduced Decarboxylative Amination Driven by Electron Donor-Acceptor Complex

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 17

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Genwei Gao, Zhen Li, Yan Li, Xi Lu. Recent Progress on the Construction of C(sp²)—C(sp³) Bonds via Photoredox/Nickel Dual Catalysis [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1905-1919.
[2]	Haoyan Wu, Mingyue He, Jun'an Ma, Faguang Zhang. Recent Advances in Photochemical Reactions Enabled by Triarylamine [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1634-1643.
[3]	Hui Li, Ablimit Abdukader, Lei Zhou. Radical Denitrogenative Ring Opening of N-Benzyl-benzotriazoles for the Synthesis of 6-Substituted Phenanthridines under Visible Light Conditions [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1770-1777.
[4]	Chen Li, Yi Jiao, Xiaoran Shi, Yiqiang Yang, Shouyun Yu. Photoredox-Catalyzed C-Glycosylation Reactions [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1423-1459.
[5]	Yang Hong, Hongping Deng. Research Progress on Photocatalyzed Protic C(sp³)—HFunctionalization [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1569-1590.
[6]	Feng Lin, Yan Zhang, Ming Wu, Huiyan Liu, Wen-Juan Hao, Bo Jiang. Visible-Light-Induced Annulative Acylative Difunctionalization of 1,6-Enynes for Accessing 1-Indanones [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1729-1738.
[7]	Xiaoqin Wang, Sheng Xu, Yuanyuan Ping, Wangqing Kong. Selective Functionalization of C(sp³)—H Bonds via Photoredox/ Nickel Dual Catalysis [J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 383-422.
[8]	Wenduo Li, Na'na Wei, Nan Feng. Boryl Radical-Promoted Synthesis of Biaryls and Benzylcarboxylic Acids Methyl Ester via C—C Bond Formation Reactions [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1853-1861.
[9]	Jiyu Liu, Shengyu Li, Kuan Chen, Yin Zhu, Yuan Zhang. Triphenylamine-Based Ordered Mesoporous Polymer as a Metal-Free Photocatalyst for Oxidation of Thiols to Disulfide [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 605-612.
[10]	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.
[11]	Chunming Gui, Tongyao Zhou, Haifeng Wang, Qiongjiao Yan, Wei Wang, Jin Huang, Fener Chen. Recent Advances in Visible Light Photoredox-Catalyzed Alkynylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2647-2663.
[12]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[13]	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.
[14]	Yadong Li, Pengju Wu, Zhiyong Yang. Synthesis of 2-Aryl Benzoxazoles from Benzoxazoles and α-Ketoic Acids by Photoredox Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1770-1777.
[15]	Tianyi Sun, Yifan Zhang, Yuanjie Meng, Yi Wang, Qifeng Zhu, Yuxin Jiang, Shihui Liu. Photoredox-Copper Dual-Catalyzed Site-Selective O-Alkylation of Glycosides [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1414-1422.