Chinese Journal of Organic Chemistry >
Electrochemical Oxidative Trifluoromethylation of α-Oxoketene Ketene Dithioacetals with CF3SO2Na
Received date: 2021-12-19
Revised date: 2022-01-04
Online published: 2022-01-21
Supported by
Natural Science Foundation of the Jiangsu Higher Education Institutions of China(21KJB150014); Large Instruments Open Foundation of Nantong University(KFJN2175); Large Instruments Open Foundation of Nantong University(KFJN2176)
An efficient electrochemical oxidative trifluoromethylation of α-oxoketene dithioacetals with CF3SO2Na is developed without the usage of transition-metal catalysts and external oxidants. This protocol features mild reaction conditions and wide functionality tolerance. Mechanistic insights indicate that the reaction proceeded via radical mechanism.
Qingyun Gu , Zhenfeng Cheng , Xiaobao Zeng . Electrochemical Oxidative Trifluoromethylation of α-Oxoketene Ketene Dithioacetals with CF3SO2Na[J]. Chinese Journal of Organic Chemistry, 2022 , 42(5) : 1537 -1544 . DOI: 10.6023/cjoc202112024
[1] | For selected reviews, see: (a) Wang, C.-S.; Dixneuf, P. H.; Soule?, J.-F. Chem. Rev. 2018, 118, 7532. |
[1] | (b) Rej, S.; Chatani, N. Angew. Chem., Int. Ed. 2019, 58, 8304. |
[1] | (c) Wang, K.; Hu, F.; Zhang, Y.; Wang, J. Sci. China Chem. 2015, 58, 1252. |
[1] | (d) Chen, X.; Xiao, F.; He, W.-M. Org. Chem. Front. 2021, 8, 5206. |
[1] | (e) Fu, X.; Zhao, W. Chin. J. Org. Chem. 2019, 39, 625. (in Chinese) |
[1] | (付晓飞, 赵文献, 有机化学, 2019, 39, 625.) |
[1] | (f) Xu, L.; Wang, F.; Chen, F.; Zhu, S.; Chu, L. Chin. J. Org. Chem. 2022, 42, 1. (in Chinese) |
[1] | (徐磊, 王方, 陈凡, 朱圣卿, 储玲玲, 有机化学, 2022, 42, 1.) |
[2] | For selected examples, see: (a) Yang, Y.-F.; Lin, J.-H.; Xiao, J.-C. Org. Lett. 2021, 23, 9277. |
[2] | (b) Huang, W.; Xu, C.; Yu, J.; Wang, M. J. Org. Chem. 2021, 86, 1987. |
[2] | (c) Lu, Z.; Hennis, O.; Gentry, J.; Xu, B.; Hammond, G. B. Org. Lett. 2020, 22, 4383. |
[2] | (d) Li, Q.; Fan, L.; Peng, D.; Meng, B.; Wang, S.; Huang, R.; Liu, S.; Li, S. ACS Catal. 2020, 10, 4012. |
[2] | (e) Lai, M.; Wu, Z.; Li, S.-J.; Wei, D.; Zhao, M. J. Org. Chem. 2019, 84, 11135. |
[2] | (f) Liang, Y.-Y.; Huang, J.; Ouyang, X.-H.; Qin, J.-H.; Song, R.-J.; Li, J.-H. Chem. Commun. 2021, 57, 3684. |
[3] | (a) Pan, L.; Bi, X.; Liu, Q. Chem. Soc. Rev. 2013, 42, 1251. |
[3] | (b) Wang, L.; He, W.; Yu, Z. Chem. Soc. Rev. 2013, 42, 599. |
[3] | (c) Xu, C.; Wang, M.; Liu, Q. Adv. Synth. Catal. 2019, 361, 1208. |
[3] | (d) Chen, J.; Yin, C.; Zhou, J.; Yu, C. Adv. Synth. Catal. 2021, 363, 4360. |
[3] | (e) Zhou, Y.; Lou, Y.; Wang, Y.; Song, Q. Org. Chem. Front. 2019, 6, 3355. |
[3] | (f) Lou, J.; Han, W.; Liu, Z.; Xiao, J. Org. Chem. Front. 2021, 8, 1447. |
[3] | (g) Huang, L.; Wu, J.; Hu, J.; Bi, Y.; Huang, D. Tetrahedron Lett. 2020, 61, 151363. |
[3] | (h) Wen, J.; Zhang, L.; Yang, X.; Niu, C.; Wang, S.; Wei, W.; Sun, X.; Yang, J.; Wang, H. Green Chem. 2019, 21, 3597. |
[3] | (i) Zhang, H.; Bao, H.; Xu, Z.; Liu, Y. Chin. J. Org. Chem. 2017, 37, 2153. (in Chinese) |
[3] | (张海峰, 鲍汉扬, 徐峥, 刘运奎, 有机化学, 2017, 37, 2153.) |
[4] | For selected reviews, see: (a) Jeschke, P.; ChemBioChem 2004, 5, 570. |
[4] | (b) Mu?ller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. |
[4] | (c) Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104, 6119. |
[4] | (d) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470. |
[4] | (e) Meanwell, N. A. J. Med. Chem. 2011, 54, 2529. |
[4] | (f) Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815. (in Chinese) |
[4] | (卿凤翎, 有机化学, 2012, 32, 815.) |
[4] | (g) Qiu, Y.; Wei, F.; Ye, L.; Zhao, M. Chin. J. Org. Chem. 2021, 41, 1821. (in Chinese) |
[4] | (邱云亮, 魏凤姣, 叶鎏, 赵旻玥, 有机化学, 2021, 41, 1821.) |
[4] | (h) Chen, D.; Yang, W.; Yao, Y.; Yang, X.; Deng, Y.; Yang, D. Chin. J. Org. Chem. 2018, 38, 2571. (in Chinese) |
[4] | (陈董涵, 杨文, 姚永祺, 杨新, 邓颖颍, 杨定乔, 有机化学, 2018, 38, 2571.) |
[5] | (a) Egami, H.; Sodeoka, M. Angew. Chem., Int. Ed. 2014, 53, 8294. |
[5] | (b) Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513. |
[5] | (c) Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598. |
[5] | (d) Barata-Vallejo, S.; Lantaño, B.; Postigo, A. Chem.-Eur. J. 2014, 20, 16806. |
[5] | (e) Alonso, C.; De Marigorta, E. M.; Rubiales, G.; Palacios, F. Chem. Rev. 2015, 115, 1847. |
[6] | Xu, C.; Liu, J.; Ming, W.; Liu, Y.; Liu, J.; Wang, M.; Liu, Q. Chem.- Eur. J. 2013, 19, 9104. |
[7] | Mao, Z.; Huang, F.; Yu, H.; Chen, J.; Yu, Z.; Xu, Z. Chem.-Eur. J. 2014, 20, 3439. |
[8] | Gou, B.; Yang, C.; Zhang, L.; Xia, W. Acta Chim. Sinica 2017, 75, 66. (in Chinese) |
[8] | (苟宝权, 杨超, 张磊, 夏吾炯, 化学学报, 2017, 75, 66.) |
[9] | For reviews on electrosynthesis, see: (a) Jutand, A. Chem. Rev. 2008, 108, 2300. |
[9] | (b) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230. |
[9] | (c) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339. |
[9] | (d) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485. |
[9] | (e) Martins, G. M.; Zimmer, G. C.; Menders, S. R.; Ahmed, N. Green Chem. 2020, 22, 4849. |
[9] | (f) Ackermann, L. Acc. Chem. Res. 2020, 53, 84. |
[9] | (g) Zhu, C.; Ang, N. W. J.; Meyer, T. H.; Qiu, Y.; Ackermann, L. ACS Cent. Sci. 2021, 7, 415. |
[9] | (h) Li, J.; Zhang, S.; Xu, K. Chin. Chem. Lett. 2021, 32, 2729. |
[9] | (i) Lian, F.; Xu, K.; Zeng, C. Chem. Rec. 2021, 21, 2290. |
[9] | (j) Meng, Z.; Feng, C.; Xu, K. Chin. J. Org. Chem. 2021, 41, 2535. (in Chinese) |
[9] | (蒙泽银, 冯承涛, 徐坤, 有机化学, 2021, 41, 2535.) |
[9] | (k) Lian, F.; Xu, K. Chin. J. Org. Chem. 2020, 40, 3490. (in Chinese) |
[9] | (廉菲, 徐坤, 有机化学, 2020, 40, 3490.) |
[10] | (a) Kisukuri, C. M.; Fernandes, V. A.; Delgado, J. A. C.; Häring, A. P.; Paixão, M. W.; Waldvogel, S. R. Chem. Rec. 2021, 21, 2502. |
[10] | (b) Zou, Z.; Zhang, W.; Wang, Y.; Pan, Y. Org. Chem. Front. 2021, 8, 2786. |
[10] | (c) Bhaskaran, R. P.; Babu, B. P. Adv. Synth. Catal. 2020, 362, 5219. |
[10] | (d) Mei, H.; Yin, Z.; Liu, J.; Sun, H.; Han, J. Chin. J. Chem. 2019, 37, 292. |
[11] | (a) Zhang, L.; Zhang, G.; Wang, P.; Li, Y.; Lei, A. Org. Lett. 2018, 20, 7396. |
[11] | (b) Liu, M.; Luo, Z.-X.; Li, T.; Xiong, D.-C.; Ye, X.-S. J. Org. Chem. 2021, 86, 16187. |
[11] | (c) Vil’, V. A.; Merkulova, V. M.; Ilovaisky, A. I.; Paveliev, S. A.; Nikishin, G. I.; Terent'ev, A. O. Org. Lett. 2021, 23, 5107. |
[11] | (d) Lin, L.; Liang, Q.; Kong, X.; Chen, Q.; Xu, B. J. Org. Chem. 2020, 85, 15708. |
[11] | (e) Claraz, A.; Courant, T.; Masson, G. Org. Lett. 2020, 22, 1580. |
[11] | (f) Hong, H.; Li, Y.; Chen, L.; Li, B.; Zhu, Z.; Chen, X.; Chen, L.; Huang, Y. J. Org. Chem. 2019, 84, 5980. |
[11] | (g) Gao, Y.; Wang, R.; Song, H.; Liu, Y.; Wang, Q. Chem. Commun. 2021, 57, 8284. |
[11] | (h) Yuan, X.; Cui, Y.-S.; Zhang, X.-P.; Qin, L.-Z.; Sun, Q.; Duan, X.; Chen, L.; Li, G.; Qiu, J.-K.; Guo, K. Chem.-Eur. J. 2021, 27, 6522. |
[11] | (i) Li, Z.; Jiao, L.; Sun, Y.; He, Z.; Wei, Z.; Liao, W.-W. Angew. Chem., Int. Ed. 2020, 59, 7266. |
[12] | Guan, Z.; Wang, H.; Huang, Y.; Wang, Y.; Wang, S.; Lei, A. Org. Lett. 2019, 21, 4619. |
[13] | Zou, Z.; Zhang, W.; Wang, Y.; Kong, L.; Karotsis, G.; Wang, Y.; Pan, Y. Org. Lett. 2019, 21, 1857. |
[14] | Zhang, Y.; Ma, C.; Struwe, J.; Feng, J.; Zhu, G.; Ackermann, L. Chem. Sci. 2021, 12, 10092. |
[15] | Zhang, S.; Li, L.; Zhang, J.; Zhang, J.; Xue, M.; Xu, K. Chem. Sci. 2019, 10, 3181. |
[16] | (a) Gu, Q.; Wang, X.; Liu, X.; Wu, G.; Xie, Y.; Shao, Y.; Zhao, Y.; Zeng, X. Org. Biomol. Chem. 2021, 19, 8295; |
[16] | (b) Zeng, X.; Wang, X.; Zhang, Y.; Zhu, L.; Zhao, Y. Org. Biomol. Chem. 2020, 18, 3734. |
[17] | Mao, Z.; Huang, F.; Yu, H.; Chen, J.; Yu, Z.; Xu, Z. Chem.-Eur. J. 2014, 20, 3439. |
[18] | Sharma, N.; Kumari, N.; Chundawat, T. S.; Kumar, S.; Bhagat, S. RSC Adv. 2017, 7, 10150. |
/
〈 |
|
〉 |