Recent Advances in Oxidative Coupling Reaction Catalyzed by Low-Valence Iodine

doi:10.6023/cjoc201805016

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (10): 2501-2518.DOI: 10.6023/cjoc201805016 Previous Articles Next Articles

Special Issue: 碳氢活化合辑2018-2019；元素有机化学合辑2018-2019

Reviews

低价碘催化的氧化偶联反应研究进展

闫溢哲^a,b, 崔畅^a, 李政^a

a 郑州轻工业学院食品与生物工程学院郑州 450000;
b 食品生产与安全河南省协同创新中心郑州 450000

收稿日期:2018-05-06 修回日期:2018-05-30 发布日期:2018-06-15
通讯作者: 闫溢哲,E-mail:yanyizhe@mail.ustc.edu.cn E-mail:yanyizhe@mail.ustc.edu.cn
基金资助:
国家自然科学基金（No.21502177）、河南省科技攻关计划（No.182102310903）和郑州轻工业学院博士研究基金（No.2014BSJJ032）资助项目.

Recent Advances in Oxidative Coupling Reaction Catalyzed by Low-Valence Iodine

Yan Yizhe^a,b, Cui Chang^a, Li Zheng^a

a School of Food and Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450000;
b Henan Collaborative Innovation Center of Food Production and Safety, Zhengzhou 450000

Received:2018-05-06 Revised:2018-05-30 Published:2018-06-15
Contact: 10.6023/cjoc201805016 E-mail:yanyizhe@mail.ustc.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21502177), the Scientific and Technological Breakthrough Plan of Henan Province (No. 182102310903) and the Doctoral Research Foundation of Zhengzhou University of Light Industry (No. 2014BSJJ032).

In recent years, low-valence iodine-catalyzed oxidative coupling reaction has made rapid progress, providing an effective method for the construction of C—C, C—O, C—N, C—S, C—P and other chemical bonds. Compared with the transition metal-catalyzed oxidation coupling reaction, this protocol is metal-free under mild conditions. It avoids the high cost and toxicity of transition metal catalyst, which meets the requirements of green chemistry. Therefore, iodine catalysis has attracted much attention of the synthetic chemists. The research progress on low-valence iodine-catalyzed oxidative coupling from 2010 to now is summarized, and outlook of this field is also prospected.

Key words: low-valence iodine, oxidative coupling, chemical bond, atom economy

Cite this article

Yan Yizhe, Cui Chang, Li Zheng. Recent Advances in Oxidative Coupling Reaction Catalyzed by Low-Valence Iodine[J]. Chin. J. Org. Chem., 2018, 38(10): 2501-2518.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2013, 52, 2.
[2] Uyanik, M.; Okamoto, H.; Yasui, T.; Ishihara, K. Science 2010, 328, 1376.
[3] Zhang, J.; Zhu, D.; Yu, C.; Wan, C.; Wang, Z. Org. Lett. 2010, 12, 2841.
[4] Chen, L.; Shi, E.; Liu, Z.; Chen, S.; Wei, W.; Li, H.; Xu, K.; Wan, X. Chem.-Eur. J. 2011, 17, 4085.
[5] Rodríguez, A.; Moran, W. J. Org. Lett. 2011, 13, 2220.
[6] Wong, Y.-C.; Tseng, C.-T.; Kao, T.-T.; Yeh, Y.-C.; Shia, K.-S. Org. Lett. 2012, 14, 6024.
[7] Li, L.-T.; Huang, J.; Li, H.-Y.; Wen, L.-J.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 5187.
[8] Li, L.-T.; Li, H.-Y.; Xing, L.-J.; Wen, L.-J.; Wang, P.; Wang, B. Org. Biomol. Chem. 2012, 10, 9519.
[9] Lu, L.; Xiong, Q.; Guo, S.; He, T.; Xu, F.; Gong, J.; Zhu, Z.; Cai, H. Tetrahedron 2015, 71, 3637.
[10] Jia, Z.; Nagano, T.; Li, X.; Chan, A. S. C. Eur. J. Org. Chem. 2013, 858.
[11] Nobuta, T.; Tada, N.; Fujiya, A.; Kariya, A.; Miura, T.; Itoh, A. Org. Lett. 2013, 15, 574.
[12] Dhineshkumar, J.; Lamani, M.; Alagiri, K.; Prabhu, K. R. Org. Lett. 2013, 15, 1092.
[13] Zhang, C.; Liu, C.; Shao, Y.; Bao, X.; Wan, X. Chem.-Eur. J. 2013, 19, 17917.
[14] Huang, H.-M.; Li, Y.-J.; Ye, Q.; Yu, W.-B.; Han, L.; Jia, J.-H.; Gao, J.-R. J. Org. Chem. 2014, 79, 1084.
[15] Tang, S.; Liu, K.; Long, Y.; Gao, X.; Gao, M.; Lei A. Org. Lett. 2015, 17, 2404.
[16] Tang, S.; Liu, K.; Long, Y.; Qi, X.; Lan, Y.; Lei, A. Chem. Commun. 2015, 51, 8769.
[17] Laha, J. K.; Jethava, K. P.; Patel, S.; Patel, K. V. J. Org. Chem. 2017, 82, 76.
[18] Shi, X.; Zhang, F.; Luo, W.-K.; Yang, L. Synlett 2016, 28, 494.
[19] Sudo, Y.; Yamaguchi, E.; Itoh, A. Org. Lett. 2017, 19, 1610.
[20] Yu, Y.; Jiao, L.; Wang, J.; Wang, H.; Yu, C.; Hao, E.; Boens, N. Chem. Commun. 2017, 53, 581.
[21] Dian, L.; Zhang-Negrerie, D.; Du, Y. Adv. Synth. Catal. 2017, 359, 3090.
[22] Wei, W.; Zhang, C.; Xu, Y.; Wan, X. Chem. Commun. 2011, 47, 10827.
[23] Uyanik, M.; Hayashi, H.; Ishihara, K. Science 2014, 345, 291.
[24] Boominathan, S. S. K.; Hu, W.-P.; Senadi, G. C.; Vandavasi, J. K.; Wang, J.-J. Chem. Commun. 2014, 50, 6726.
[25] Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2011, 50, 5331.
[26] Guo, S.; Yu, J.-T.; Dai, Q.; Yang, H.; Cheng, J. Chem. Commun. 2014, 50, 6240.
[27] Gao, W.-C.; Hu, F.; Huo, Y.-M.; Chang, H.-H.; Li, X.; Wei, W.-L. Org. Lett. 2015, 17, 3914.
[28] Liang, Y.-F.; Li, X.; Wang, X.; Zou, M.; Tang, C.; Liang, Y.; Song, S.; Jiao, N. J. Am. Chem. Soc. 2016, 138, 12271.
[29] Zhang, S.; Guo, L.-N.; Wang, H.; Duan, X.-H. Org. Biomol. Chem. 2013, 11, 4308.
[30] Yu, H.; Shen, J. Org. Lett. 2014, 16, 3204.
[31] Feng, J.; Liang, S.; Chen, S.-Y.; Zhang, J.; Fu, S.-S.; Yu, X.-Q. Adv. Synth. Catal. 2012, 354, 1287.
[32] Huang, J.; Li, L.-T.; Li, H.-Y.; Husan, E.; Wang P.; Wang, B. Chem. Commun. 2012, 48, 10204.
[33] Liu, L.; Yun, L.; Wang, Z.; Fu, X.; Yan, C.-H. Tetrahedron Lett. 2013, 54, 5383.
[34] Majji, G.; Guin, S.; Gogoi, A.; Rout, S. K.; Patel, B. K. Chem. Commun. 2013, 49, 3031.
[35] Xu, J.; Zhang, P.; Li, X.; Gao, Y.; Wu, J.; Tang, G.; Zhao, Y. Adv. Synth. Catal. 2014, 356, 3331.
[36] Xiong, B.; Wang, G.; Zhou, C.; Liu, Y.; Zhang, P.; Tang, K. J. Org. Chem. 2018, 83, 993.
[37] Shi, E.; Shao, Y.; Chen, S.; Hu, H.; Liu, Z.; Zhang, J.; Wan, X. Org. Lett. 2012, 14, 3384.
[38] Froehr, T.; Sindlinger, C. P.; Kloeckner, U.; Finkbeiner, P.; Nachtsheim, B; J. Org. Lett. 2011, 13, 3754.
[39] Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2013, 15, 5226.
[40] Beukeaw, D.; Udomsasporn, K.; Yotphan, S. J. Org. Chem. 2015, 80, 3447.
[41] Yang, Z.-Y.; Tian, T.; Du, Y.-F.; Li, S.-Y.; Chu, C.-C.; Chen, L.-Y.; Li, D.; Liu, J.-Y.; Wang, B. Chem. Commun. 2017, 53, 8050.
[42] Liu, Z.; Zhang, J.; Chen, S.; Shi, E.; Xu, Y.; Wan, X. Angew. Chem., Int. Ed. 2012, 51, 3231.
[43] Xu, K.; Hu, Y.; Zhang, S.; Zha, Z.; Wang, Z. Chem.-Eur. J. 2012, 18, 9793.
[44] Li, H.; Xie, J.; Xue, Q.; Cheng, Y.; Zhu, C. Tetrahedron Lett. 2012, 53, 6479.
[45] Gao, L.; Tang, H.; Wang, Z. Chem. Commun. 2014, 50, 4085.
[46] Tan, B.; Toda, N.; Barbas Ⅲ, C. F. Angew. Chem., Int. Ed. 2012, 51, 12538.
[47] Wang, G.; Yu, Q.-Y.; Chen, S.-Y.; Yu, X.-Q. Org. Biomol. Chem. 2014, 12, 414.
[48] Zhao, J.; Li, P.; Xia, C.; Li, F. Chem. Commun. 2014, 50, 4751.
[49] Zhang, X.; Wang, L. Green Chem. 2012, 14, 2141.
[50] Wei, W.; Shao, Y.; Hu, H.; Zhang, F.; Zhang, C.; Xu, Y.; Wan, X. J. Org. Chem. 2012, 77, 7157.
[51] Mai, W.-P.; Wang, H.-H.; Li, Z.-C.; Yuan, J.-W.; Xiao, Y.-M.; Yang, L.-R.; Mao, P.; Qu, L.-B. Chem. Commun. 2012, 48, 10117.
[52] Zhao, Q.; Miao, T.; Zhang, X.; Zhou, W.; Wang, L. Org. Biomol. Chem. 2013, 11, 1867.
[53] Lamani, M.; Prabhu, K. R. Chem.-Eur. J. 2012, 18, 14638.
[54] Tian, J.-S.; Jeffrey Ng, K. W.; Wong, J.-R.; Loh, T.-P. Angew. Chem., Int. Ed. 2012, 51, 9105.
[55] Ma, L.; Wang, X.; Yu, W.; Han, B. Chem. Commun. 2011, 47, 11333.
[56] Xie, J.; Jiang, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2012, 48, 979.
[57] Yan, Y.; Zhang, Y.; Zha, Z.; Wang, Z. Org. Lett. 2013, 15, 2274.
[58] Yu, H.; Huang, W.; Zhang, F. Eur. J. Org. Chem. 2014, 3156.
[59] Ilangovan, A.; Satish, G. J. Org. Chem. 2014, 79, 4984.
[60] Yan, Y.; Zhang, Y.; Feng, C.; Zha, Z.; Wang, Z. Angew. Chem., Int. Ed. 2012, 51, 8077.
[61] Lao, Z.-Q.; Zhong, W.-H.; Lou, Q.-H.; Li, Z.-J.; Meng, X.-B. Org. Biomol. Chem. 2012, 10, 7869.
[62] Zheng, Y.; Mao, J.; Chen, J.; Rong, G.; Liu, D.; Yan, H.; Chi, Y.; Xu, X. RSC Adv. 2015, 5, 50113.
[63] Yan, Y.; Xu, Y.; Niu, B.; Xie, H.; Liu, Y. J. Org. Chem. 2015, 80, 5581.
[64] Sun, K.; Wang, X.; Li, G.; Zhu, Z.; Jiang, Y.; Xiao, B. Chem. Commun. 2014, 50, 12880.
[65] Rajamanickam, S.; Majji, G.; Santra, S. K.; Patel, B. K. Org. Lett. 2015, 17, 5586.
[66] Yan, Y.; Li, Z.; Li, H.; Cui, C.; Shi, M.; Liu, Y. Org. Lett. 2017, 19, 6228.
[67] Luo, Z.; Jiang, Z.; Jiang, W.; Lin, D. J. Org. Chem. 2018, 83, 3710.
[68] Xue, Q.; Xie, J.; Li, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 3700.
[69] Zhao, D.; Wang, T.; Shen, Q.; Li, J.-X. Chem. Commun. 2014, 50, 4302.
[70] Zhao, D.; Shen, Q.; Li, J.-X. Adv. Synth. Catal. 2015, 357, 339.
[71] Huang, H.; Chen, W.; Xu, Y.; Li, J. Green Chem. 2015, 17, 4715.
[72] Luo, W.-K.; Shi, X.; Zhou, W.; Yang, L. Org. Lett. 2016, 18, 2036.
[73] Zhang, X.; Wang, M.; Li, P.; Wang, L. Chem. Commun. 2014, 50, 8006.
[74] Tang, S.; Wu, Y.; Liao, W.; Bai, R.; Liu, C.; Lei, A. Chem. Commun. 2014, 50, 4496.
[75] Xiao, F.; Chen, H.; Xie, H.; Chen, S.; Yang, L.; Deng, G.-J. Org. Lett. 2014, 16, 50.
[76] Siddaraju, Y.; Prabhu, K. R. J. Org. Chem. 2017, 82, 3084.
[77] Zhao, J.; Huang, H.; Wu, W.; Chen, H.; Jiang, H. Org. Lett. 2013, 15, 2604.
[78] Liao, Y.; Jiang, P.; Chen, S.; Qi, H.; Deng, G.-J. Green Chem. 2013, 15, 3302.
[79] Cao, H.; Yuan, J.; Liu, C.; Hu, X.; Lei, A. RSC Adv. 2015, 5, 41493.
[80] Jiang, Y.; Zou, J.-X.; Huang, L.-T.; Peng, X.; Deng, J.-D.; Zhu, L.-Q.; Yang, Y.-H.; Feng, Y.-Y.; Zhang, X.-Y.; Wang, Z. Org. Biomol. Chem. 2018, 16, 1641.
[81] Yuan, J.; Ma, X.; Yi, H.; Liu, C.; Lei, A. Chem. Commun. 2014, 50, 14386.
[82] Xiao, F.; Chen, S.; Chen, Y.; Huang, H.; Deng, G.-J. Chem. Commun. 2015, 51, 652.
[83] Li, X.; Xu, X.; Zhou, C. Chem. Commun. 2012, 48, 12240.
[84] Wang, Q.; Xu, Z. Chin. J. Org. Chem. 2013, 33, 2430(in Chinese). (王倩, 徐洲, 有机化学, 2013, 33, 2430.)
[85] Sun, K.; Lv, Y.; Chen, Y.; Zhou, T.; Xing, Y.; Wang, X. Org. Biomol. Chem. 2017, 15, 4464.
[86] Dhineshkumar, J.; Prabhu, K. R. Org. Lett. 2013, 15, 6062.
[87] Wang, J.; Huang, X.; Ni, Z.; Wang, S.; Wu, J.; Pan, Y. Green Chem. 2015, 17, 314.
[88] Yuan, J.; Liu, C.; Lei, A. Org. Chem. Front. 2015, 2, 677.
[89] Zhang, J.; Jiang, J.; Li, Y.; Wan, X. J. Org. Chem. 2013, 78, 11366.
[90] Yan, Y.; Niu, B.; Xu, K.; Yu, J.; Zhi, H.; Liu, Y. Adv. Synth. Catal. 2016, 358, 212.
[91] Feng, J.-B.; Wu, X.-F. Org. Biomol. Chem. 2016, 14, 6951.

低价碘催化的氧化偶联反应研究进展

Recent Advances in Oxidative Coupling Reaction Catalyzed by Low-Valence Iodine

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wenting Wei, Zhuangzhuang Li, Wandi Li, Jiaqi Li, Xianying Shi. Green Method for Constructing Phthalides via Oxidative Coupling of Aromatic Acids and Acrylates in Neat Water and Air [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1177-1186.
[2]	Binghao Huo, Conghui Guo, Zhanhui Xu. Mn(acac)₃ Promoted Radical Oxidative Coupling Reaction of Enol Esters with Phosphites to Synthesize β-Ketophosphonates [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3989-3996.
[3]	Jianming Zhao, Jiashun Zhu, Jiabin Shen, Yilan Zhang, Wanmei Li. Photocatalyzed Oxidative Cross-Coupling Reaction to Access Symmetrical/Unsymmetrical Thiosulfonates [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2940-2946.
[4]	Bangkui Yu, Hanmin Huang. Recent Advances in C—X Bond Metathesis Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2376-2389.
[5]	Xiaoshuang Ji, Rong Fu, Shuliang Wang, Wenjuan Hao, Bo Jiang. Visible-Light-Driven Photocatalytic Kharasch Reaction of Phenol/ Arylamine-Linked 1,6-Enynes with Perhalogenated Methane [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4282-4291.
[6]	Junfeng Qian, Xiaoting Tian, Zhong Wu, Jie Yao, Hui Wang, Weiyou Zhou. Efficient Oxidative Coupling of Isochroman with Primary Arylamines Catalyzed by Heterogeneous Ni-Containing Layered Double Oxide [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3668-3674.
[7]	Wei Chen, Qiang Liu. Recent Advances in the Oxidative Coupling Reaction of Enol Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3414-3430.
[8]	Yang Zhenhua, Zhu Jianan, Wen Caiyue, Ge Yingxiang, Zhao Shengyin. Recent Advances in Functionalization of Double Bond Based on Maleimides [J]. Chin. J. Org. Chem., 2019, 39(9): 2412-2427.
[9]	Chen Wei, Guo Renyu, Gong Jianxian, Yang Zhen. Diastereoselective Construction of All-Carbon Quaternary Stereocenters via Intramolecular Oxidative Cross-Coupling Reaction [J]. Chin. J. Org. Chem., 2019, 39(1): 238-248.
[10]	Liu Hong, Dong Huiru, An Rui, Tang Yu, Xu Kaitian, Zhang Yuanming. Synthesis of 1,3-Diaryl or Dialkyl-2H-isoindole-4,7-dione via Barbier-Grignard-Type Reaction [J]. Chin. J. Org. Chem., 2018, 38(8): 2008-2016.
[11]	Li Changsheng, Zou Yulong, Jia Changqing, Qin Zhaohai, Ma Yongqiang. Synthesis and Fungicidal Activity of Bridging Ligand Compounds of Azo with 1, 3, 5-Substitued Triazole [J]. Chin. J. Org. Chem., 2018, 38(6): 1500-1506.
[12]	Xu Lige, Huang Yi, Liu Binggen, Niu Yunhong, Huo Xing. Progress in Oxidative Coupling Reaction of Olefins, Alkynes and Aromatic Hydrocarbons Catalyzed by Palladium [J]. Chin. J. Org. Chem., 2018, 38(4): 812-824.
[13]	Chen Liang, Wang Baoqu, Zhao Yucheng, Yan Shengjiao, Lin Jun. One-Pot Synthesis of Multisubstituted Chromone-Fused Bicyclic Pyridine Compounds [J]. Chin. J. Org. Chem., 2017, 37(6): 1433-1442.
[14]	Wang Baoqu, Kong Lingbin, Luo Qin, Lin Jun, Yan Shengjiao. One-Step Synthesis of Isoquinolinone Compounds [J]. Chin. J. Org. Chem., 2017, 37(11): 2972-2977.
[15]	Wang Jian, Cui Dongmei. Research Progress in Non-noble Metals Catalyzed Hydroamination of Alkyenes and Alkynes [J]. Chin. J. Org. Chem., 2016, 36(6): 1163-1183.