N-Iodo-succininide (NIS)/K2S2O8 Initiated Self-Coupling of Enamides to Nitrogen-Containing Quaternary Carbon Centers

doi:10.6023/cjoc202003032

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2142-2147.DOI: 10.6023/cjoc202003032 Previous Articles Next Articles

N-碘代丁二酰亚胺(NIS)/K₂S₂O₈促进烯酰胺的自偶联反应构建含氮原子的季碳中心

周小强^a,b, 闫浩^b,c, 王秋亚^a

a 渭南师范学院化学与材料学院陕西渭南 714099;
b 兰州大学功能有机分子化学国家重点实验室兰州 730000;
c 陕西中医药大学药学院陕西咸阳 712046

收稿日期:2020-03-12 修回日期:2020-03-29 发布日期:2020-04-17
通讯作者: 周小强 E-mail:zhouxq2017@163.com
基金资助:
陕西省科技厅自然科学基础研究基金（No.2019JQ-902）、陕西省教育厅自然科学专项研究基金（No.19JK0287）和渭南师范学院博士科研启动基金（Nos.18ZRRC05，17ZRRC04）资助项目.

N-Iodo-succininide (NIS)/K₂S₂O₈ Initiated Self-Coupling of Enamides to Nitrogen-Containing Quaternary Carbon Centers

Zhou Xiaoqiang^a,b, Yan Hao^b,c, Wang Qiuya^a

a College of Chemistry and Material, Weinan Normal University, Weinan, Shaanxi 714099;
b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000;
c College of pharmacy, Shaanxi University of Chinese Medicine, Xianyang, Shaanxi 712046

Received:2020-03-12 Revised:2020-03-29 Published:2020-04-17
Supported by:
Project supported by the Natural Science Basic Research Program of Shaanxi Province (No. 2019JQ-902), the Scientific Research Program Funded by Shaanxi Provincial Education Department (No. 19JK0287), and the Scientific Research Foundation of Weinan Normal University (Nos. 18ZRRC05, 17ZRRC04).

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Abstract

N-Iodo-succininide (NIS)/K₂S₂O₈ initiated C-C bond formation reaction through self-coupling of enamides has been reported. The environmental friendliness and high atom-economy of this transition-metal free radical pathway offers a useful and attractive strategy to nitrogen-containing quaternary carbon centers.

Key words: quaternary carbon centers, enamides, C-C bond formation, iodide, radical addition, transition-metal free

Cite this article

Zhou Xiaoqiang, Yan Hao, Wang Qiuya. N-Iodo-succininide (NIS)/K₂S₂O₈ Initiated Self-Coupling of Enamides to Nitrogen-Containing Quaternary Carbon Centers[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2142-2147.

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[1] For reviews, see (a) Fuji, K. Chem. Rev. 1993, 93, 2037.
(b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
(c) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591.
(d) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
[2] (a) Ohfune, Y.; Shinada, T., Eur. J. Org. Chem. 2005, 5127.
(b) Cordell, G. A. The Alkaloids:Chemistry and Biology, Vol. 60, Elsevier, San Diego, 2003.
(c) Ramon, D. J.; Yus, M. Curr. Org. Chem. 2004, 8, 149.
(d) Kobayashi, J.; Morita, H. Alkaloids 2003, 60, 165.
[3] (a) Wang, Q.-S.; Xie, J.-H.; Li, W.; Zhu, S.-F.; Wang, L.-X.; Zhou, Q.-L. Org. Lett. 2011, 13, 3388.
(b) Zhang, Q.; Zhu, S.-F.; Qiao, X.-C.; Wang, L.-X.; Zhou, Q.-L. Adv. Synth. Catal. 2008, 350, 1507.
[4] Guan, Z.-H.; Zhang, Z.; Ren, Z.; Wang, Y.; Zhang, X.-M. J. Org. Chem. 2011, 76, 339.
[5] (a) Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585.
(b) Stuart, D.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326.
(c) Zhao, M.; Ren, Z.; Wang, Y.; Guan, Z.-H. Chem. Commun. 2012, 48, 8105.
(d) Chen, M.; Ren, Z.; Wang, Y.; Guan, Z.-H. Angew. Chem., Int. Ed. 2013, 52, 14196.
(e) Zhao, M.; Ren, Z.; Wang, Y.; Guan, Z.-H. Chem.-Eur. J. 2014, 20, 1839.
(f) Zhao, M.; Ren, Z.; Wang, Y.; Guan, Z.-H. Org. Lett. 2014, 16, 608.
(g) Li, B.; Wang, N.; Liang, Y.; Xu, S.; Wang, B. Org. Lett. 2013, 15, 136.
(h) Li, Y.; Zhou, X.; Wu, Z.; Cao, J.; Ma, C.; He, Y.; Huang, G. RSC Adv. 2015, 5, 88214.
(i) Cao, J.; Zhou, X.; Ma, H.; Shi, C.; Huang, G. RSC Adv. 2016, 6, 57232. (j) Zhao, M.-N.; Ren, Z.-H.; Yang, D.-S.; Guan, Z.-H. Org. Lett. 2018, 20, 1287.
(k) Chang, X.-H.; Wang, Z.-L.; Zhao, M.; Yang. C.; Li, J.-J.; Ma, W.-W.; Xu, Y.-H. Org. Lett. 2020, 22, 944.
[6] Zhou, X.; Yan, H.; Ma, C.; He, Y.; Li, Y.; Cao, J.; Yan R.; Huang, G. J. Org. Chem. 2016, 81, 25.
[7] Liu, R.-H.; Shen, Z.-Y.; Wang, C.; Loh, T.-P.; Hu, X.-H. Org. Lett. 2020, 22, 944.
[8] (a) Kobayashi, S.; Gustafsson, T.; Shimizu, Y.; Kiyohara, H.; Matsubara, R. Org. Lett. 2006, 8, 4923.
(b) Matsubara, R.; Vital, P.; Nakamura, Y.; Kiyohara, H.; Kobayashi, S. Tetrahedron 2004, 60, 9769.
[9] Jia, Y.; Zhong, J.; Zhu, S.; Zhang, C.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2007, 46, 5565.
[10] Baudequin, C.; Zamfir, A.; Tsogoeva, S. B. Chem. Commun. 2008, 4637.
[11] Zhao, M.; Du, W.; Ren, Z.; Wang, Y.; Guan, Z.-H. Eur. J. Org. Chem. 2013, 7989.
[12] (a) Wu, X.; Gong, J.; Qi, X. Org. Biomol. Chem. 2014, 12, 5807.
(b) Shi, Z.; Wang, L.; Cui, X. Chin. J. Org. Chem. 2019, 39, 1596(in Chinese). (施兆江, 王连会, 崔秀灵, 有机化学, 2019, 39, 1596.)
[13] Tian, Y.; Sun, C.; Tan, R.-X.; Liu, Z.-Q. Green Chem. 2018, 20, 588.

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N-碘代丁二酰亚胺(NIS)/K₂S₂O₈促进烯酰胺的自偶联反应构建含氮原子的季碳中心

N-Iodo-succininide (NIS)/K₂S₂O₈ Initiated Self-Coupling of Enamides to Nitrogen-Containing Quaternary Carbon Centers

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N-碘代丁二酰亚胺(NIS)/K2S2O8促进烯酰胺的自偶联反应构建含氮原子的季碳中心