Chinese Journal of Organic Chemistry >
Recent Progress in N-Iodosuccinimide (NIS)-Mediated Iodination Reactions
Received date: 2023-06-28
Revised date: 2023-09-18
Online published: 2023-10-12
Supported by
National Natural Science Foundation of China(21702043); Hebei Provincial Natural Science Foundation(B2021201035)
Organoiodine compounds belong to a very important class of functional molecules and their synthesis research is of great significance. Given the advantages of N-iodosuccinimide (NIS) with high reactivity, cheap and easy to get and environmental friendliness, it has always been the preferred iodine reagent for iodization, and in recent years, the preparation of organic iodine compounds by iodization reaction with NIS has made great progress, which has received considerable interest. To this end, the research progress is summarized, including the C—H iodization of NIS and aromatics/terminal alkynes, iodine difunctionalization between NIS and unsaturated compounds with nucleophiles, and cascade iodocyclization between NIS and unsaturated compounds.
Key words: iodization; N-iodosuccinimide; organoiodine compounds
Tongyang Cao , Wei Li , Lijing Wang . Recent Progress in N-Iodosuccinimide (NIS)-Mediated Iodination Reactions[J]. Chinese Journal of Organic Chemistry, 2024 , 44(2) : 508 -524 . DOI: 10.6023/cjoc202306026
| [1] | (a) Wang, L.; Zhou, X.; Fredimoses, M.; Liao, S.; Liu, Y. RSC Adv. 2014, 4, 57350. |
| [1] | (b) Gribble G. W. Mar. Drug. 2015, 13, 4044. |
| [2] | Vekariya, R. H.; Balar, C. R.; Sharma, V. S.; Prajapati, N. P.; Vekariya, M. K.; Sharma, A. S. ChemistrySelec. 2018, 3, 9189. |
| [3] | (a) Frontier, A.; Leboeuf, D.; Ciesielski, J. Synlet. 2013, 25, 399. |
| [3] | (b) Kambe, N.; Iwasaki, T.; Terao, J. Chem. Soc. Rev. 2011, 40, 4937. |
| [4] | Racys, D. T.; Warrilow, C. E.; Pimlott, S. L.; Sutherland, A. Org. Lett. 2015, 17, 4782. |
| [5] | Gohier, F.; Grolleau, J.; Frère, P. Synthesi. 2015, 47, 3901. |
| [6] | Xiong, H. X.; Yao, M.; Zhang, J. J.; Yang, S.; Liu, E. Synlet. 2020, 31, 1102. |
| [7] | Gu, S.-X.; Qiao, H.; Sun, K.; Duan, T.; Ju, X.-L. Chem. Reag. 2014, 36, 988 (in Chinese). |
| [7] | (古双喜, 乔恒, 孙克, 段婷, 巨修练, 化学试剂. 2014, 36, 988.) |
| [8] | Cant, A. A.; Champion, S.; Bhalla, R.; Pimlott, S. L.; Sutherland, A. Angew. Chem.. Int. Ed. 2013, 52, 7829. |
| [9] | Yang, H.; Li, Y.; Jiang, M.; Wang, J.; Fu, H. Chem. Eur. J. 011, 17, 5652. |
| [10] | Filimonov, V. D.; Trusova, M.; Postnikov, P.; Krasnokutskaya, E. A.; Lee, Y. M.; Hwang, H. Y.; Kim, H.; Chi, K. W. Org. Lett. 2008, 10, 3186. |
| [11] | Prakash, G. K. S.; Mathew, T.; Dushyanthi, H.; Esteves, P. M.; Wang, Q.; Rasul, G.; Olah, G. A. J. Am. Chem. Soc. 2004, 126, 15770. |
| [12] | Zhou, C. Y.; Li, J.; Peddibhotla, S.; Romo, D. Org. Lett. 2010, 12, 2107. |
| [13] | Frontier, A.; Leboeuf, D.; Ciesielski, J. Synlet. 2013, 25, 399. |
| [14] | Racys, D. T.; Sharif, S. A.; Pimlott, S. L.; Sutherland, A. J. Org. Chem. 2016, 81, 772. |
| [15] | Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Org. Lett. 2006, 8, 2523. |
| [16] | (a) Schroder, N.; Wencel-Delord, J.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 8298. |
| [16] | (b) Wang, L.; Ackermann, L. Chem. Commun. 2014, 50, 1083. |
| [16] | (c) Qiu, F.-C.; Yang, W.-C.; Chang, Y.-Z.; Guan, B.-T. Asian J. Org. Chem. 2017, 6, 1361. |
| [17] | Gupta, S.; Melanson, J. A.; Vaillancourt, L.; Nugent, W. A.; Tanoury, G. J.; Schatte, G.; Snieckus, V. Org. Lett. 2018, 20, 3745. |
| [18] | Ma, X.-T.; Tian, S.-K. Adv. Synth. Catal. 2013, 355, 337. |
| [19] | Wu, J. J.; He, D. Z.; Zhang, L.; Liu, Y. D.; Mo, X. G.; Lin, J. B.; Zhang, H. J. Org. Lett. 2017, 19, 5438. |
| [20] | Erbing, E.; Sanz-Marco, A.; Vázquez-Romero, A.; Malmberg, J.; Johansson, M. J.; Gómez-Bengoa, E.; Martín-Matute, B. ACS Catal. 2018, 8, 920. |
| [21] | Zheng, D. S.; Zhang, W. W.; Gu, Q.; You, S. L. ACS Catal. 2023, 13, 5127. |
| [22] | Huestis M. P. J. Org. Chem. 2016, 81, 12545. |
| [23] | Wang, Z. Y.; Guo, R. L.; Zhang, X. L.; Wang, M. Y.; Chen, G. N.; Wang, Y. Q. Org. Chem. Front. 2021, 8, 1844. |
| [24] | Yang, C.-Y.; Hu, L.-P.; Zhang, D.-R.; Li, X.; Teng, M.-Y.; Liu, B.; Huang, G.-L. New J. Chem. 2022, 46, 10934. |
| [25] | (a) Zeng, X. J.; Liu, S. W.; Shi, Z. Y.; Xu, B. Org. Lett. 2016, 18, 4770. |
| [25] | (b) Mader, S.; Molinari, L.; Rudolph, M.; Rominger, F.; Hashmi, A. S. Chem.-Eur. J. 2015, 21, 3910. |
| [26] | (a) Naskar, D.; Roy, S. J. Org. Chem. 1999, 64, 6896. |
| [26] | (b) Das, J. P.; Roy, S. J. Org. Chem. 2002, 67, 7861. |
| [26] | (c) Starkov, P.; Rota, F.; D'Oyley, J. M.; Sheppard, T. D. Adv. Synth. Catal. 2012, 354, 3217. |
| [27] | Shi, W.; Guan, Z.; Cai, P.; Chen, H. J. Catal. 2017, 353, 199. |
| [28] | Li, M.; Li, Y.; Zhao, B.; Liang, F.; Jin, L.-Y. RSC Adv. 2014, 4, 30046. |
| [29] | Yao, M.; Zhang, J. J.; Yang, S.; Xiong, H. X.; Li, L.; Liu, E.; Shi, H. RSC Adv. 2020, 10, 3946. |
| [30] | Berini, C.; Lavergne, A.; Molinier, V.; Capet, F.; Deniau, E.; Aubry, J.-M. Eur. J. Org. Chem. 2013, 2013, 1937. |
| [31] | Zhang, Z.; Chang, L.; Wang, S.; Wang, H.; Yao, Z.-J. RSC Adv. 2013, 3, 18446. |
| [32] | Zhu, L. L.; Xu, X. Q.; Shi, J. W.; Chen, B. L.; Chen, Z. L. J. Org. Chem. 2016, 81, 3568. |
| [33] | Sun, K.; Luan, B. X.; Liu, Z. H.; Zhu, J. L.; Du, J. K.; Bai, E. Q.; Fang, Y.; Zhang, B. Org. Biomol. Chem. 2019, 17, 4208. |
| [34] | Li, H.-H.; Li, X.-X.; Zhao, Z.-G.; Lin, C.-B.; Ma, T.; Sun, C.-Y.; Yang, B.-W.; Fu, X.-L. Tetrahedron Lett. 2016, 57, 4640. |
| [35] | Re He Man, X. J. A. T.; Liu, Y. C.; Li, X. X.; Zhao, Z. G. New J. Chem. 2019, 43, 14739. |
| [36] | Tan, Y.; Jia, S.; Hu, F.; Liu, Y.; Peng, L.; Li, D.; Yan, H. J. Am. Chem. Soc. 2018, 140, 16893. |
| [37] | Wang, Q. L.; Zheng, N. Org. Lett. 2019, 21, 9999. |
| [38] | Xiong, B.; Xu, S.; Zhu, Y.; Yao, L.; Zhou, C.; Liu, Y.; Tang, K. W.; Wong, W. Y. Chem.-Eur. J. 2020, 26, 9556. |
| [39] | Chu, D.; Ellman, J. A. Org. Lett. 2022, 24, 2921. |
| [40] | Faizi, S.; Farooqi, F.; Zikr-Ur-Rehman, S.; Naz, A.; Noor, F.; Ansari, F.; Ahmad, A.; Khan, S. A. Tetrahedro. 2009, 65, 998. |
| [41] | Crone, B.; Kirsch, S. F. Org. Lett. 2007, 72, 5435. |
| [42] | (a) Jiang, X. P.; Fu, C. L.; Ma, S. M. Chem.-Eur. J. 2008, 14, 9656. |
| [42] | (b) Lu, B.; Jiang, X. P.; Fu, C. L.; Ma, S. M. J. Org. Chem. 2009, 74, 438. |
| [43] | Pradal, A.; Nasr, A.; Toullec, P. Y.; Michelet, V. Org. Lett. 2010, 12, 5222. |
| [44] | (a) Jurberg, L. D.; Gagosz, F.; Zard, S. Z. Org. Lett. 2010, 12, 416. |
| [44] | (b) Zhu, Y. X.; Yin, G. W.; Hong, D.; Lu P.; Wang, Y. G. Org. Lett. 2011, 13, 1024. |
| [44] | (c) Fujioka, H.; Maehata, R.; Wakamatsu, S.; Nakahara, K.; Hayashi, T.; Oki, T. Org. Lett. 2012, 14, 1054. |
| [44] | (d) Zhang, L.; Zhu, Y.; Yin, G.; Lu, P.; Wang, Y. J. Org. Chem. 2012, 77, 9510. |
| [44] | (e) Raffa, G.; Balme, G.; Monteiro, N. Eur. J. Org. Chem. 2013, 2013, 105. |
| [45] | Huber, F.; Kirsch, S. F. J. Org. Chem. 2013, 78, 2780. |
| [46] | Shen, Z.; Pan, X.; Lai, Y.; Hu, J.; Wan, X.; Li, X.; Zhang, H.; Xie, W. Chem. Sci. 2015, 6, 6986. |
| [47] | Li, Y.-L.; Li, J.; Yu, S.-N.; Wang, J.-B.; Yu, Y.-M.; Deng, J. Tetrahedro. 2015, 71, 8271. |
| [48] | Sasaki, T.; Miyagi, K.; Moriyama, K.; Togo, H. Org. Lett. 2016, 18, 944. |
| [49] | Sasaki, T.; Moriyama, K.; Togo, H. J. Org. Chem. 2017, 82, 11727. |
| [50] | Wu, Y. M.; Zhang, J. M.; Guo, Y. W.; Wang, X. J.; Zhu, Z. T. Synlet. 2016, 27, 2259. |
| [51] | Song, Y.; Wang, L. C.; Du, S.; Chen, Z.; Wu, X. F. Org. Biomol. Chem. 2021, 19, 6115. |
| [52] | Fedoseev, P.; Coppola, G.; Ojeda, G. M.; Van der Eycken, E. V. Chem. Commun. 2018, 54, 3625. |
| [53] | Kondoh, A.; Aita, K.; Ishikawa, S.; Terada, M. Org. Lett. 2020, 22, 2105. |
| [54] | Velasco, N.; Martínez‐Nú?ez, C.; Fernández‐Rodríguez, M. A.; Sanz, R.; Suárez‐Pantiga, S. Adv. Synth. Catal. 2022, 364, 2932. |
| [55] | Cao, T. Y.; Qi, L.; Dong, W.; Yan, Z. M.; Ji, S. C.; Du, J. L.; Zhang, L.; Li, W.; Wang, L. J. J. Org. Chem. 2022, 87, 16578. |
| [56] | Cao, T. Y.; Qi, L.; Wang, L. J. J. Org. Chem. 2023, 88, 3035. |
| [57] | Liu, T.; Mei, T. S.; Yu, J. Q. J. Am. Chem. Soc. 2015, 137, 5871. |
| [58] | Wang, A. F.; Zhu, Y. L.; Wang, S. L.; Hao, W. J.; Li, G.; Tu, S. J.; Jiang, B. J. Org. Chem. 2016, 81, 1099. |
| [59] | Ni, S. Y.; Cao, J.; Mei, H. B.; Han, J. L.; Li, S. H.; Pan, Y. Green Chem. 2016, 18, 3935. |
| [60] | Li, X.; Ding, Y.; Qian, L.; Gao, Y.; Wang, X.; Yan, X.; Xu, X. J. Org. Chem. 2019, 84, 12656. |
| [61] | Zou, L.; Wang, L.; Sun, L.; Xie, X. F.; Li, P. H. Chem. Commun. 2020, 56, 7933. |
| [62] | Yang, M.; Hua, J. W.; Wang, H.; Ma, T.; Liu, C. K.; He, W.; Zhu, N.; Hu, Y. J.; Fang, Z.; Guo, K. J. Org. Chem. 2022, 87, 8445. |
| [63] | Ariyarathna, J. P.; Baskaran, P.; Chhikara, A.; Kaur, N.; Nguyen, A. M.; Premathilaka, S. M.; Huynh, M. M.; Truong, J. T.; Li, W. Chem. Commun. 2023, 59, 6418. |
/
| 〈 |
|
〉 |