Chinese Journal of Organic Chemistry >
Electrochemical Oxidated-Iodide Promoted α-H Aryl(alkyl)selenation of Acetone for the Preparation of α-Aryl(alkyl)selenoacetones
Received date: 2021-02-08
Revised date: 2021-03-20
Online published: 2021-06-08
Supported by
Natural Science Foundation of Hunan Province(2019JJ40392); Natural Science Foundation of Hunan Province(2019JJ50193)
α-Aryl(alkyl)selenyl ketones have been important intermediates in organic transformation. Here, a new route to α-aryl (alkyl) selenoacetones via the electrochemical oxidated iodide promoted α-H aryl(alkyl)selenation of acetone by using stable and easy available diaryl(alkyl)diselenides as selenide reagent is reported. Comparing to the previous methods, this strategy has the advantages of mild reaction conditions, high atom economy and wide functional groups tolerance, providing an efficient and green route to α-aryl (alkyl) selenoacetones.
Rongnan Yi , Dongxian Liu , Qilin Wu , Mingming Zhao , Yong Wang , Zheng Wang . Electrochemical Oxidated-Iodide Promoted α-H Aryl(alkyl)selenation of Acetone for the Preparation of α-Aryl(alkyl)selenoacetones[J]. Chinese Journal of Organic Chemistry, 2021 , 41(9) : 3726 -3732 . DOI: 10.6023/cjoc202102024
| [1] | Kolonko, K. J.; Wherritt, D. J.; Reich, H. J. J. Am. Chem. Soc. 2011, 133, 16774. |
| [2] | Mukherjee, A. J.; Zade, S. S.; Singh, H. B.; Sunoj, R. B. Chem. Rev. 2010, 110, 4357. |
| [3] | Mugesh, G.; du Mont, W. W.; Sies, H. Chem. Rev. 2001, 101, 2125. |
| [4] | Chen, J. Y.; Wu, H. Y.; Gui, Q. W.; Yan, S. S.; Deng, J.; Lin, Y. W.; Cao, Z.; He, W. M. Chin. J. Catal. 2021, 42, 1445. |
| [5] | Nian, H.; Bisson, W. H.; Dashwood, W.-M.; Pinto, J. T.; Dashwood, R. H. Carcinogenesis 2009, 30, 1416. |
| [6] | Chen, Z.; Lai, H.; Hou, L.; Chen, T. Chem. Commun. 2020, 56, 179. |
| [7] | Mukherjee, A. J.; Zade, S. S.; Singh, H. B.; Sunoj, R. B. Chem. Rev. 2010, 110, 4357. |
| [8] | Doering, M.; Ba, L. A.; Lilienthal, N.; Nicco, C.; Scherer, C.; Abbas, M.; Zada, A. A. P.; Coriat, R.; Burkholz, T.; Wessjohann, L.; Diederich, M.; Batteux, F.; Herling, M.; Jacob, C. J. Med. Chem. 2010, 53, 6954. |
| [9] | Dunlap, T. L.; Howell, C. E.; Mukand, N.; Chen, S. N.; Pauli, G. F.; Dietz, B. M.; Bolton, J. L. Chem. Res. Toxicol. 2017, 30, 2084. |
| [10] | Guo, P.; Wang, Q.; Liu, J.; Liu, L.; Zhao, P.; Cao, Y.; Liu, Y.; Qi, C. Biol. Trace Elem. Res. 2013, 154, 304. |
| [11] | Yu, Y.; Jin, Y.; Zhou, J.; Ruan, H.; Zhao, H.; Lu, S.; Zhang, Y.; Li, D.; Ji, X.; Ruan, B. H. ACS Chem. Biol. 2017, 12, 3003. |
| [12] | Desai, D.; Salli, U.; Vrana, K. E.; Amin, S. Bioorg. Med. Chem. Lett. 2010, 20, 2044. |
| [13] | Pinto, J. T.; Sinha, R.; Papp, K.; Facompre, N. D.; Desai, D.; El-Bayoumy, K. Int. J. Cancer 2007, 120, 1410. |
| [14] | Liao, L.; Guo, R.; Zhao, X. Angew. Chem. Int. Ed. 2017, 129, 3201. |
| [15] | Zeni, G.; Alves, D.; Pena, J. M.; Braga, A. L.; Stefani, H. A.; Nogueira, C. W. Org. Biomol. Chem. 2004, 35, 803. |
| [16] | Sharma, S.; Pathare, R. S.; Maurya, A. K.; Gopal, K.; Roy, T. K.; Sawant, D. M.; Pardasani, R. T. Org. Lett. 2016, 47, 356. |
| [17] | Wang, Y.; Yu, L.; Zhu, B.; Yu, L.; J. Mater. Chem. A 2016, 4, 10828. |
| [18] | Pandaa, S.; Pandaa, A.; Zade, S. S. Coord. Chem. Rev. 2015, 300, 86. |
| [19] | Yang, D.; Gao, Q.; Zheng, B. F.; Zhu, N. Y. J. Org. Chem. 2004, 69, 8821. |
| [20] | Pandey, G.; Tiwari, S. K.; Budakoti, A.; Sahani, P. K. Org. Chem. Front. 2018, 5, 2610. |
| [21] | Temperinia, A.; Siciliano, C. Tetrahedron 2020, 76, 131311. |
| [22] | Attanasi, O. A.; De Crescentini, L.; Mantellinia, F.; Marinib, F.; Nicolinia, S.; Sternativob, S.; Tiecco, M. Synlett 2009, 1118. |
| [23] | Yan, G.; Borah, A. J.; Wang, Li.; Pan, Z.; Chen, S.; Shen, X.; Wu, X. Tetrahedron Lett. 2015, 56, 4305. |
| [24] | Ouyang, Y.; Guo, C.; Qiu, R.; Li, N.; Chen, J.; Xu, X. Chin. J. Org. Chem. 2015, 35, 731. (in Chinese). |
| [24] | ( 欧阳跃军, 郭翠霞, 邱仁华, 李宁波, 陈锦杨, 许新华, 有机化学, 2015, 35, 731.) |
| [25] | Wang, J.; Li, H.; Mei, Y.; Lou, B.; Xu, D;. Xie, D.; Guo, H.; Wang, W. J. Org. Chem. 2005, 70, 5678. |
| [26] | Victoria, F. N.; Radatz, C. S.; Sachini, M.; Jacob, R. G.; Perin, G.; da Silva, W. P.; Lenardão, E. J. Tetrahedron Lett. 2009, 50, 6761. |
| [27] | Wang, J.; Li, H.; Mei, Y.; Lou, B.; Xu, D.; Xie, D.; Guo, H.; Wang, W. J. Org. Chem. 2005, 70, 5678. |
| [28] | Yang, M. H.; Wang, H. S.; Zheng, Y. F.; Zhu, C. J. Chin. J. Org. Chem. 2006, 26, 1268. (in Chinese). |
| [28] | ( 杨明华, 王红松, 郑云法, 朱成建, 有机化学, 2006, 26, 1268.) |
| [29] | Yang, X. Y.; Wang, R.; Wang, L.; Li, J.; Mao, S.; Zhang, S. Q.; Chen, N. RSC Adv. 2020, 10, 28902. |
| [30] | Movassagh, M. N. Tetrahedron Lett. 2009, 50, 1453. |
| [31] | Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27. |
| [32] | Shi, S.-H.; Liang, Y.; Jiao, N. Chem. Rev. 2020, 121, 485. |
| [33] | Kingston, C.; Palkowitz, M. D.; Takahira, Y.; Vantourout, J. C.; Peters, B. K.; Kawamata, Y.; Baran, P. S. Acc. Chem. Res. 2020, 53, 72. |
| [34] | Zhou, Y.; Zhao, Z.; Zeng, L.; Li, M.; He, Y.; Gu, L. Chin. J. Org. Chem. 2021, 41, 1072. (in Chinese). |
| [34] | ( 周娅琴, 赵志恒, 曾亮, 李鸣, 何永辉, 谷利军, 有机化学, 2020 41, 1072.) |
| [35] | Zeng, L.; Li, J.; Gao, J.; Huang, X.; Wang, W.; Zheng, X.; Gu, L.; Li, G.; Zhang, S.; He, Y. Green Chem. 2020, 22, 3416. |
| [36] | Zhao, Z.; Li, M.; Zhou, Y.; He, Y.; Zhang, L.; Li, G.; Gu, L. Chin. J. Org. Chem. 2020, 41, 2476. (in Chinese). |
| [36] | ( 赵志恒, 李鸣, 周娅琴, 何永辉, 张丽珠, 李干鹏, 谷利军, 有机化学, 2020, 41, 2476.) |
| [37] | Zuo, H.-D.; Hao, W.-J.; Zhu, C.-F.; Guo, C.; Tu, S.-J.; Jiang, B. Org. Lett. 2020, 22, 4471. |
| [38] | Jiang, J.; Wang, Z.; He, W. M. Chin. Chem. Lett. 2021, 32, 1591. |
| [39] | Wang, X. Y.; Xu, X. T.; Wang, Z. H.; Fang, P.; Mei, T. S. Chin. J. Org. Chem. 2020, 40, 3738. (in Chinese). |
| [39] | ( 王向阳, 徐学涛, 王振华, 方萍, 梅天胜, 有机化学, 2020, 40, 3738.) |
| [40] | Xu, P.; Chen, P. Y.; Xu, H. C. Angew. Chem. Int. Ed. 2020, 59, 14275. |
| [41] | Chen, J. Y.; Wu, H. Y.; Gui, Q. W.; Han, X. R.; Wu, Y.; He, W. M. Org. Lett. 2020, 22, 2206. |
| [42] | Cao, Z. C.; Liu, J. C.; Chu, Y. Q.; Zhao, F. M.; Zhu, Y. H.; She, Y. B. Chin. J. Org. Chem. 2019, 39, 2499. (in Chinese). |
| [42] | ( 曹志成, 刘建超, 褚有群, 赵峰鸣, 朱英红, 佘远斌, 有机化学, 2019, 39, 2499.) |
| [43] | Pan, C.; Liu, P.; Wu, A. G.; Li, M.; Wen, L. R.; Guo, W. S. Chin. J. Org. Chem. 2020, 40, 2855. (in Chinese). |
| [43] | ( 潘超, 刘鹏, 武安国, 李明, 文丽荣, 郭维斯, 有机化学, 2020, 40, 2855.) |
| [44] | Li, M. F.; Wang, R.; Hao, W. J.; Jiang, B. Chin. J. Org. Chem. 2020, 40, 1540. (in Chinese). |
| [44] | ( 李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2020, 40, 1540.) |
| [45] | Chen, J. Y.; Zhong, C. T.; Gui, Q. W.; Zhou, Y. M.; Fang, Y. Y.; Liu, K. J.; Lin, Y. W.; Cao, Z.; He, W. M. Chin. Chem. Lett. 2021, 32, 475. |
| [46] | Leng, T.; Wu, G.; Zhou, Y. B.; Gao, W.; Ding, J.; Huang, X.; Liu, M.; Wu, H. Adv. Synth. Catal. 2018, 360, 4336. |
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