Synthesis of Heteroatom-Bridged Six-Membered Cyclic Diaryliodonium Salts

doi:10.6023/cjoc202502029

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (10): 3838-3846.DOI: 10.6023/cjoc202502029 Previous Articles Next Articles

ARTICLES

杂原子桥联六元环状二芳基碘盐的合成

焦善延, Khan Hamza, 王利民, 韩建伟^*()

华东理工大学化学与分子工程学院精细化工系上海市功能性材料化学重点实验室上海 200237

收稿日期:2025-02-24 修回日期:2025-05-23 发布日期:2025-06-06
基金资助:
国家自然科学基金(22478117)

Synthesis of Heteroatom-Bridged Six-Membered Cyclic Diaryliodonium Salts

Shanyan Jiao, Khan Hamza, Limin Wang, Jianwei Han^*()

Shanghai Key Laboratory of Functional Materials Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237

Received:2025-02-24 Revised:2025-05-23 Published:2025-06-06
Contact: * jianweihan@ecust.edu.cn
Supported by:
National Natural Science Foundation of China(22478117)

1. .pdf(7990KB)

Abstract

A synthetic method for heteroatom-bridged cyclic diaryliodonium salts by using ortho-substituted functionalized diaryliodonium salts is presented. Coumarin skeleton was also incorporated into cyclic diaryliodonium salts. UV-Visible absorption of these cyclic diaryliodonium salts was performed to demonstrate their potential applications in photo-chemistry.

Key words: diaryliodonium salts, hypervalent iodine chemistry, cyclic diaryliodonium salts, coumarin

Cite this article

Shanyan Jiao, Khan Hamza, Limin Wang, Jianwei Han. Synthesis of Heteroatom-Bridged Six-Membered Cyclic Diaryliodonium Salts[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3838-3846.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

Scheme 1. Synthesis of cyclic diaryliodonium salts

Table 1. Substrate expansion of oxygen-bridged six-membered cyclic diaryliodonium saltsa,b

Table 2. Substrate expansion of N-bridged heterocyclic diaryliodonium saltsa,b

Scheme 2. Further transformations of coumarin-based cyclic diaryliodonium salts Reaction conditions: diaryliodonium salts 2aj/2ak (0.5 mmol, 1 equiv.), Pd/C (0.0025 mmol, 0.05 equiv.) and NaOAc (1.5 mmol, 3 equiv.) in 5 mL of DMA, 140 ℃, 24 h. Isolated yield after column chromatography.

Figure 1. UV-Vis absorption spectra for product 2aj, 2ak, 2aj', and 2ak' (c=10 μmol/L in MeCN)

References 10

[1]	(a) Yang, X. G.; Hu, Z. N.; Jia, M. C.; Du, F. H.; Zhang, C. Synlett 2021, 32, 1289. pmid: 26861673
	(b) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328. doi: 10.1021/acs.chemrev.5b00547 pmid: 26861673
	(c) Zhang, B.; Li, X.; Guo, B.; Du, Y. Chem. Commun. 2020, 56, 14119. pmid: 26861673
	(d) Wang, Y.; An, G.; Wang, L.; Han, J. Curr. Org. Chem. 2020, 24, 2070. doi: 10.2174/1385272824999200507124328 pmid: 26861673
	(e) Pan, C.; Wang, L.; Han, J. Chem. Rec. 2023,23, e202300138. pmid: 26861673
	(f) Ma, X.; Li, K.; Wu, S.; Liang, C.; Su, G.; Mo, D. Green Chem. 2017, 56, 5761. pmid: 26861673
	(g) Duan, Y.; Jiang, S.; Han, Y.; Sun, B.; Zhang, C. Chin. J. Org. Chem. 2016, 36, 1973 (in Chinese). pmid: 26861673
	(段亚南, 姜山, 韩永超, 孙博, 张弛, 有机化学, 2016, 36, 1973.) doi: 10.6023/cjoc201605007 pmid: 26861673
	(h) Ma, J. L.; Chen, L. C.; Yuan, Z. W.; Cheng, H. C. Chin. J. Org. Chem. 2018, 38, 1586 (in Chinese). pmid: 26861673
	(马姣丽, 陈立成, 袁中文, 程辉成, 有机化学, 2018, 38, 1586.) doi: 10.6023/cjoc201802021 pmid: 26861673
	(i) Sun, Y. Y.; Song, J. C.; Qin, Q. X.; Zhang, E. X.; Han, Q. Q; Yang, S. H.; Wang, Z. L.; Yue, S.; Dong, D. Q. Chin. J. Org. Chem. 2021, 41, 4651 (in Chinese). pmid: 26861673
	(孙媛媛, 宋敬城, 秦启学, 张恩选, 韩晴晴, 杨少慧, 王祖利, 岳姗, 董道青, 有机化学, 2021, 41, 4651.) doi: 10.6023/cjoc202106006 pmid: 26861673
[2]	(a) Chatterjee, N.; Goswami, A. Eur. J. Org. Chem. 2017, 21, 3023.
	(b) Zhu, D.; Peng, H.; Sun, Y.; Wu, Z.; Wang, Y.; Luo, B.; Yu, T.; Hu, Y.; Huang, P.; Wen, S. Green Chem. 2021, 23, 1972.
	(c) Ma, J. L.; Zhou, X. M.; Chen, J. L.; Xu, S. Q.; Li, X. T.; Cheng, H. C. J. Guangdong Univ. Petrochem. Technol. 2022, 32, 17 (in Chinese).
	(马姣丽, 周旭明, 陈嘉琳, 许少倩, 李晓桐, 程辉成, 广东石油化工学院学报, 2022, 32, 17.)
[3]	(a) Carroll, M. A.; Pike, V. W.; Widdowson, D. A. Tetrahedron Lett. 2000, 41, 5393. pmid: 34995468
	(b) Bielawski, M.; Olofsson, B. Chem. Commun. 2007, 2521. pmid: 34995468
	(c) Bielawski, M.; Aili, D.; Olofsson, B. J. Org. Chem. 2008, 73, 4602. doi: 10.1021/jo8004974 pmid: 34995468
	(d) Pan, C.; Wang, L.; Han, J. Org. Lett. 2020, 22, 4776. pmid: 34995468
	(e) Liu, X.; Wang, L.; Han, J. Org. Biomol. Chem. 2022, 20, 8628. pmid: 34995468
	(f) Pan, C.; Wang, L.; Han, J. Adv. Synth. Catal. 2022, 364, 268. pmid: 34995468
	(g) Yang, S.; Wang, F.; Wu, Y.; Hua, W.; Zhang, F. Org. Lett. 2018, 20, 1491. pmid: 34995468
	(h) Lei, L.; Zou, P.; Wang, Z.; Liang, C.; Hou, C.; Mo, D. Org. Lett. 2022, 24, 663. doi: 10.1021/acs.orglett.1c04120 pmid: 34995468
	(i) Nie, S.; Zhang, X.; Wang, Z.; Su, G.; Pan, C.; Mo, D. Adv. Synth. Catal. 2022, 364, 3782. pmid: 34995468
[4]	Kikushima, K.; Elboray, E. E.; Jiménez-Halla, J. O. C.; Solorio Alvarado, C. R.; Dohi, T. Org. Biomol. Chem. 2022, 20, 3231.
[5]	(a) Vlasenko, Y. A.; Kuczmera, T. J.; Antonkin, N. S.; Valiev, R. R.; Postnikov, P. S.; Nachtsheim, B. J. Adv. Synth. Catal. 2023, 364, 535.
	(b) Wang, M.; Chen, S.; Jiang, X. Chem. Asian J. 2018, 13, 2195.
	(c) Peng, X.; Rahim, A.; Peng, W.; Jiang, F.; Gu, Z.; Wen, S. Chem. Rev. 2023, 123, 1364.
	(d) Cheng, H.; Ma, J.; Guo, P. Adv. Synth. Catal. 2023, 365, 1112.
	(e) Yoshimura, A.; Saito, A.; Zhdankin, V. V. Adv. Synth. Catal. 2023, 365, 2653.
	(f) Singhal, R.; Choudhary, S. P.; Malik, B.; Pilania, M. Org. Biomol. Chem. 2023, 21, 4358.
[6]	Beringer, F. M.; Kravetz, L.; Topliss, G. B. J. Org. Chem. 1965, 30, 1141.
[7]	(a) Luo, B.; Cui, Q.; Luo, H.; Hu, Y.; Huang, P.; Wen, S. Adv. Synth. Catal. 2016, 358, 2733.
	(b) Reinhard, D. L.; Heinen, F.; Stoesser, J.; Engelage, E.; Huber, S. M. Helv. Chim. Acta 2021,104, e202100221.
[8]	Damrath, M.; Caspers, L. D.; Duvinage, D.; Nachtsheim, B. J. Org. Lett. 2022, 24, 2562.
[9]	(a) Linde, E.; Knippenberg, N.; Olofsson, B. Chem.-Eur. J. 2022,28, e202202453.
	(b) Linde, E.; Bulfield, D.; Kervefors, G.; Purkait, N.; Olofsson, B. Chem 2022, 8, 850.
[10]	(a) Chen, H.; Han, J.; Wang, L. Angew. Chem., Int. Ed. 2018, 57, 12313.
	(b) Chen, H.; Han, J.; Wang, L. Org. Lett. 2020, 22, 3581.
	(c) Chen, H.; Han, J.; An, L. G.; Sun, X.; Li, X.; Liu, Y.; Zhao, S.; Wang, L. J. Chem. Educ. 2021, 98, 3992.
	(d) Wang, Y.; Zhang, Y.; Wang, L.; Han, J. Asian J. Org. Chem. 2021,11, e202100669.

[1]	Xuxin Chen, Dandan Zhang, Hongxin Long, Guokai Liu. Ready Synthesis of 3-Difluoromethylated Coumarins Enabled by Photosensitizer-Free Photoinduced Radical Difluoromethylation of Alkynoates [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1739-1746.
[2]	Mengqin Liu, Yiting Chen, Juyuan Zhang, Heye Zhou, Tao Qin, Bin Liu. Efficient Synthesis of Diaryl Sulfides via Three Component Cross Coupling [J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1283-1296.
[3]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.
[4]	Jiling Yi, Kangqi Shi, Binglin Wu, Wanshan Li, Guangying Chen. Study on Secondary Metabolites of Marine-Derived Fungus Eutypella sp. F0219 [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 295-298.
[5]	Mianyuan Wu, Yanchao Yu, Yang Liu, Jun You, Wenju Wu, Bo Liu. Synthesis and Application of a Novel Fluorescent Probe for Sequential Recognition Cu²⁺ and Glyphosate [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 803-811.
[6]	Yamin Sun, Xiyong Li, Jinwei Yuan, Jialin Yu, Shuainan Liu. CuI-Catalyzed Regioselective Synthesis of 3-Arylcoumarins with Arylamines under Mild Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 631-640.
[7]	Mingzhou Shang, Lanlan Zhang, Miaomiao Chen, Wangcheng Hu, Xinwei He, Hongjian Lu. Synthesis of Esterified/Fused Isocoumarins via Rh-Catalyzed C—H Activation/Transannulative Coupling/Annulation of Phthalic Anhydrides with Cyclic 2-Diazo-1,3-diketones and Methanol [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3816-3823.
[8]	Jin Cai, Xuhua Nong, Bin Wang, Weinü Zeng, Guolei Huang, Ziyi Zhang, Caijuan Zheng. Three New Polyketides from the Culture of Mangrove-Derived FungusEupenicilliumsp. HJ002 [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2905-2909.
[9]	Xiaoyu Yang, Jianlin Liu, Fangzhi Hu, Hongmei Sun, Liang Wang, Shuai-Shuai Li. Diverse Application of 4-Hydroxycoumarin in the Syntheses of Tetrahydroquinoline and Zwitterionic Biscoumarin Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2788-2799.
[10]	Chenglu Zhang, Yanpeng Zhang, Huayu Wang, Huanying Zhao, Meitong Shang, Lu Zhang, Xiangling Li, Yiming Wang. Synthesis and Application of Triazolothiadiazole-Coumarin Based Ratiometric Fluorescent Probes for Highly Selective Detection of H₂S [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2384-2392.
[11]	Xiang Wang, Ping Chen, Sanjun Zhi, Huayou Hu, Yuhe Kan, Guodong Tang, Zaichao Zhang. Synthesis of 3-Benzo[d]imidazol-2(3H)-ylidene Substituted Pyrano-[3,2-c]chromen-2-ones via Three-Component Reaction [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1241-1245.
[12]	Xianjiao Meng, Jinzhong Zhao, Yongpo Zhang, Zhichun Li, Changchun Yuan, Wenbing Ma. A Fluorescent Chemosensor Based on Coumarin for Squential Recognition of Al³⁺ and Pyrophosphate (PPi) in Aqueous Solution [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1161-1167.
[13]	Yuqian Dai, Xingwei Li, Bingxian Liu. Rh(III)-Catalyzed Efficient Synthesis of Isocoumarins from Cyclohexanediones [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4476-4483.
[14]	Min Zhao, Fei Li, Yizheng Cheng, Youming Wang, Zhenghong Zhou. Optically Active 3,4-Dihydrocoumarins via Organocatalyzed Asymmetric [4+2] Annulation of ortho-Hydroxyl Functionalized p-Quinone Methides with β-Keto Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4039-4049.
[15]	Yuhe Qiu, Kanghui Lu, Bangchi Wei, Zhenkai Qian, Zhengjie He. P^III-Mediated Intramolecular Cyclopropanation and Synthesis of Cyclopropa[c]coumarins [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4066-4074.

杂原子桥联六元环状二芳基碘盐的合成

Synthesis of Heteroatom-Bridged Six-Membered Cyclic Diaryliodonium Salts

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 10

Related Articles 15

Recommended Articles

Metrics

Comments