Advances on Nitrogen-centered Radical Chemistry:A Photocatalytic N-H Bond Activation Approach

doi:10.6023/A17080384

Acta Chim. Sinica ›› 2017, Vol. 75 ›› Issue (12): 1137-1149.DOI: 10.6023/A17080384 Previous Articles Next Articles

Review

氮自由基化学新进展:光催化N-H键活化途径

宋颢, 刘小宇, 秦勇

靶向药物与释药系统教育部重点实验室华西药学院四川大学成都 610041

投稿日期:2017-08-23 发布日期:2017-09-29
通讯作者: 秦勇,E-mail:yongqin@scu.edu.cn E-mail:yongqin@scu.edu.cn
作者简介:宋颢博士于1981年生于成都.2003年毕业于四川大学华西药学院获学士学位;2006年在四川大学华西药学院获理学硕士学位;2009年在四川大学华西药学院获理学博士学位,同年9月任四川大学讲师,2013年任副教授.目前主要从事具有重要生理活性的天然产物的全合成及药物化学研究;刘小宇博士于1985年生于四川.2006年毕业于四川大学华西药学院获学士学位;2012年在四川大学华西药学院获理学博士学位;2012年至2014年在韩国首尔大学进行博士后研究,2014年至今,任四川大学华西药学院副研究员.目前主要从事基于天然产物的目标导向和多样性导向合成研究;秦勇博士于1967年生于云南.1989毕业于云南大学化学系获学士学位;1995年在中国科学院化学研究所获理学博士学位;1996年至2000年,美国佛蒙特大学化学系做博士后;2000年至2003年,美国圣地亚哥生物制药公司Triad Therapeutics Inc.公司任研究科学家;2003年至今,任四川大学华西药学院教授.目前主要从事具有重要生理活性的天然产物的全合成及药物化学研究.
基金资助:
项目受国家自然科学基金（Nos.21572140，21732005）和科技部重大新药专项（No.2017ZX09101005-009-002）资助.

Advances on Nitrogen-centered Radical Chemistry:A Photocatalytic N-H Bond Activation Approach

Song Hao, Liu Xiaoyu, Qin Yong

Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, China

Received:2017-08-23 Published:2017-09-29
Contact: 10.6023/A17080384 E-mail:yongqin@scu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572140, 21732005) and the National Science and Technology Major Projects for "Major New Drugs Innovation and Development" (No. 2017ZX09101005-009-002).

Nitrogen-centered radicals are highly reactive intermediates, which provide new opportunities for designing new chemical reactions and preparing nitrogen-containing molecules. Direct generation of nitrogen-centered radicals via activation of N-H bonds under photocatalytic conditions has emerged as a green, efficient, and economical process, where significant progress has been made with methodology development in very recent years. In this paper, we highlight the important advances in this area that were reported since 2016.

Key words: nitrogen-centered radical, visible light, photocatalyst, single-electron transfer, cascade reaction

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Song Hao, Liu Xiaoyu, Qin Yong. Advances on Nitrogen-centered Radical Chemistry:A Photocatalytic N-H Bond Activation Approach[J]. Acta Chim. Sinica, 2017, 75(12): 1137-1149.

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References

[1] For selected reviews on the N-radical chemistry, see:
(a) Zard, S. Z. Chem. Soc. Rev. 2008, 37, 1603.
(b) Stella, L. In Radicals in Organic Synthesis, Vol. 2, Eds.: Renaud, P.; Sibi, M. P., Wiley, New York, 2001, p. 407.
(c) Quiclet-Sire, B.; Zard, S. Z. Beilstein J. Org. Chem. 2013, 9, 557.
[2] For selected examples, see:
(a) Lessard, J.; Cote, R.; Mackiewicz, P.; Furstoss, R.; Waegell, B. J. Org. Chem. 1978, 43, 3750.
(b) Boivin, J.; Fouquet, E.; Schiano, A.-M.; Zard, S. Z. Tetrahedron 1994, 50, 1769.
(c) Gennet, D.; Zard, S. Z.; Zhang, H. Chem. Commun. 2003, 1870.
(d) Lu, H.; Li, C. Tetrahedron Lett. 2005, 46, 5983.
(e) Guin, J.; Fröhlich, R.; Studer, A. Angew. Chem. Int. Ed. 2008, 47, 779.
[3] For selected examples, see:
(a) Sherman, E. S.; Chemler, S. R.; Tan, T. B.; Gerlits, O. Org. Lett. 2004, 6, 1573.
(b) Sherman, E. S.; Fuller, P. H.; Kasi, D.; Chemler, S. R. J. Org. Chem. 2007, 72, 3896.
(c) Zeng, W.; Chemler, S. R. J. Am. Chem. Soc. 2007, 129, 12948.
(d) Zhu, X.; Wang, Y.-F.; Ren, W.; Zhang, F.-L.; Chiba, S. Org. Lett. 2013, 15, 3214.
(e) Zhu, M.-K.; Chen, Y.-C.; Loh, T. P. Chem. Eur. J. 2013, 19, 5250.
(f) Duan, X.-Y.; Zhou, N.-N.; Fang, R.; Yang, X.-L.; Yu, W.; Han, B. Angew. Chem. Int. Ed. 2014, 53, 3158.
(g) Duan, X. Y.; Yang, X. L.; Jia, P. P.; Zhang, M.; Han, B. Org. Lett. 2015, 17, 6022.
[4] For selected reviews on the visible light photocatalysis, see:
(a) Xuan, J.; Xiao, W.-J. Angew. Chem. Int. Ed. 2012, 51, 6828.
(b) Shi, L.; Xia, W.-J. Chem. Soc. Rev. 2012, 41, 7687.
(c) Prier, C. K.; Rankic, D. A.; Macmillan, D. W. Chem. Rev. 2013, 113, 5322.
(d) Xi, Y.-M.; Yi, H.; Lei, A.-W. Org. Biomol. Chem. 2013, 11, 2387.
(e) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 985.
(f) Xuan, J.; Zhang, Z.-G.; Xiao, W.-J. Angew. Chem. Int. Ed. 2015, 54, 15632.
(g) Karkas, M. D.; Porco Jr., J. A.; Stephenson, C. R. Chem. Rev. 2016, 116, 9683.
(h) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
(i) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Acc. Chem. Res. 2016, 49, 1911.
(j) Liu, Y.; Song, R.; Li, J. Sci. China Chem. 2016, 59, 161.
(k) Zhang, J.; Chen, Y. Acta Chim. Sinica 2017, 75, 41(in Chinese). (张晶, 陈以昀, 化学学报, 2017, 75, 41.)
(l) Chen, J.-R.; Yan, D.-M.; Wei, Q.; Xiao, W.-J. ChemPhotoChem 2017, 1, 148.
[5] For recent reviews, see:
(a) Chen, J.-R.; Hu, X. Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2016, 45, 2044.
(b) Xiong, T.; Zhang, Q. Chem. Soc. Rev. 2016, 45, 3069.
(c) Gentry, E. C.; Knowles, R. R. Acc. Chem. Res. 2016, 49, 1546.
(d) Nguyen, L. Q.; Knowles, R. R. ACS Catal. 2016, 6, 2894.
(e) Kärkäs, M. D. ACS Catal. 2017, 7, 4999.
[6] For recent reviews, see:
(a) Gensch, T.; Hopkinson, M. N.; Glorius, F.; Wencel-Delord, J. Chem. Soc. Rev. 2016, 45, 2900.
(b) Zhu, R.-Y.; Farmer, M. E.; Chen, Y.-Q.; Yu, J.-Q. Angew. Chem. Int. Ed. 2016, 55, 10578.
(c) Della Ca', N.; Fontana, M.; Motti, E.; Catellani, M. Acc. Chem. Res. 2016, 49, 1389.
(d) He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J.-Q. Chem. Rev. 2017, 117, 8754.
[7] For selected examples, see:
(a) Qin, Q.; Yu, S. Org. Lett. 2015, 17, 1894.
(b) Hollister, K. A.; Conner, E. S.; Spell, M. L.; Deveaux, K.; Maneval, L.; Beal, M. W.; Ragains, J. R. Angew. Chem. Int. Ed. 2015, 54, 7837.
(c) Huang, F.-Q.; Dong, X.; Qi, L.-W.; Zhang, B. Tetrahedron Lett. 2016, 57, 1600.
(d) Zhang, J.; Li, Y.; Zhang, F.; Hu, C.; Chen, Y. Angew. Chem. Int. Ed. 2016, 55, 1872.
(e) Wang, C.; Harms, K.; Meggers, E. Angew. Chem. Int. Ed. 2016, 55, 13495.
(f) Shaaban, S.; Oh, J.; Maulide, N. Org. Lett. 2016, 18, 345.
(g) Parasram, M.; Chuentragool, P.; Sarkar, D.; Gevorgyan, V. J. Am. Chem. Soc. 2016, 138, 6340.
(h) Hu, X.-Q.; Chen, J.-R.; Xiao, W.-J. Angew. Chem. Int. Ed. 2017, 56, 1960.
[8] Choi, G. J.; Zhu, Q.; Miller, D. C.; Gu, C. J.; Knowles, R. R. Nature 2016, 539, 268.
[9] Chu, J. C. K.; Rovis, T. Nature 2016, 539, 272.
[10] Zhang, L.; Meggers, E. Acc. Chem. Res. 2017, 50, 320.
[11] Zhou, Z.; Li, Y.; Han, B.; Gong, L.; Meggers, E. Chem. Sci. 2017, 8, 5757.
[12] Yuan, W.; Zhou, Z.; Gong, L.; Meggers, E. Chem. Commun. 2017, 53, 8964.
[13] For a recent review, see: Huang, L.; Arndt, M.; Gooßen, K.; Heydt, H.; Gooßen, L. J. Chem. Rev. 2015, 115, 2596.
[14] Musacchio, A. J.; Lainhart, B. C.; Zhang, X.; Naguib, S. G.; Sherwood, T. C.; Knowles, R. R. Science 2017, 355, 727.
[15] For a recent review, see: Chen, Z.-M.; Zhang, X.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2015, 44, 5220.
[16] Shu, W.; Genoux, A.; Li, Z.; Nevado, C. Angew. Chem. Int. Ed. 2017, 56, 10521.
[17]
(a) Hu, X.-Q.; Chen, J.-R.; Wei, Q.; Liu, F.-L.; Deng, Q.-H.; Beauchemin, A. M.; Xiao, W.-J. Angew. Chem. Int. Ed. 2014, 53, 12163.
(b) Hu, X.-Q.; Qi, X.; Chen, J.-R.; Zhao, Q.-Q.; Wei, Q.; Lan, Y.; Xiao, W.-J. Nat. Commun. 2016, 7, 11188.
(c) Zhao, Q.-Q.; Hu, X.-Q.; Yang, M.-N.; Chen, J.-R.; Xiao, W.-J. Chem. Commun. 2016, 52, 12749.
(d) Hu, X.-Q.; Chen, J.; Chen, J.-R.; Yan, D.-M.; Xiao, W.-J. Chem. Eur. J. 2016, 22, 14141.
(e) Zhao, Q.-Q.; Chen, J.; Yan, D.-M.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2017, 19, 3620.
(f) Yu, X.; Zhou, F.; Chen, J.; Xiao, W. Acta Chim. Sinica 2017, 75, 86(in Chinese). (余晓叶, 周帆, 陈加荣, 肖文精, 化学学报, 2017, 75, 86.)
[18] Tong, K.; Liu, X.; Zhang, Y.; Yu, S. Chem. Eur. J. 2016, 22, 15669.
[19] Ito, E.; Fukushima, T.; Kawakami, T.; Murakami, K.; Itami, K. Chem 2017, 2, 383.
[20]
(a) Zhao, Y.; Huang, B.; Yang, C.; Xia, W. Org. Lett. 2016, 18, 3326.
(b) Zhao, Y.; Huang, B.; Yang, C.; Li, B.; Gou, B.; Xia, W. ACS Catal. 2017, 7, 2446.
[21] Wang, X.; Xia, D.; Qin, W.; Zhou, R.; Zhou, X.; Zhou, Q.; Liu, W.; Dai, X.; Wang, H.; Wang, S.; Tan, L.; Zhang, D.; Song, H.; Liu, X.-Y.; Qin, Y. Chem 2017, 2, 803.

氮自由基化学新进展:光催化N-H键活化途径

Advances on Nitrogen-centered Radical Chemistry:A Photocatalytic N-H Bond Activation Approach

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