SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 11: 3697 - 3713

DOI: https://doi.org/10.6023/cjoc202004045

综述与进展

可见光与钯协同催化的有机合成化学

  • 周文俊 ,
  • 蒋元旭 ,
  • 陈亮 ,
  • 刘开兴 ,
  • 余达刚
展开
  • a 内江师范学院化学化工学院 四川内江 641100;
    b 四川大学化学学院 绿色化学与技术教育部重点实验室 成都 610064

收稿日期: 2020-04-28

  修回日期: 2020-05-21

  网络出版日期: 2020-05-29

基金资助

国家自然科学基金（Nos.21801176，21772129）、国家重点基础研究发展规划（973计划）（No.2015CB856600）、四川省科技厅计划（No.2019YJ0379）和内江师范学院开放课题（No.KF10076）资助项目.

收起

Visible-Light Photoredox and Palladium Dual Catalysis in Organic Synthesis

  • Zhou Wenjun ,
  • Jiang Yuanxu ,
  • Chen Liang ,
  • Liu Kaixing ,
  • Yu Dagang
Expand
  • a College of Chemistry and Chemical Engineering, Neijiang Normal University, Neijiang, Sichuan 641100;
    b Key Laboratory of Green Chemistry&Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064

Received date: 2020-04-28

  Revised date: 2020-05-21

  Online published: 2020-05-29

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21801176, 21772129), the National Basic Research Program of China (973 Program) (No. 2015CB856600), the Sichuan Science and Technology Program (No. 2019YJ0379) and the Open Project of Neijiang Normal University (No. KF10076).

Fold

摘要

钯催化的有机转化反应是金属有机化学的一个重要分支.由于其可以高效构建碳-碳键和碳-杂键，钯催化在合成化学、材料科学和医药工业等领域具有广泛应用，但其中部分反应存在条件苛刻（如需要高温、使用强碱）等不足.另一方面，可见光催化反应利用可见光作为能量来源，通过产生高活性的反应中间体，在温和条件下实现了许多常规热反应条件下不能实现的化学转化，但也存在反应类型和底物范围有限等问题.针对这两个领域各自存在的问题，人们通过结合可见光催化和钯催化，利用光敏剂与有机钯络合物之间的电子转移或能量转移，在温和条件下高效高选择性地实现了一系列新颖的有机转化，具有广谱的底物适用范围和良好的应用前景.在这些转化中，可见光催化与钯催化既各司其职，又相互协作，缺一不可.以不同反应类型为主线，总结了近年来可见光和钯协同催化的有机合成化学研究进展，并分析了该领域未来的重点研究方向.

关键词： 可见光催化; 钯催化; 协同催化; 有机合成

本文引用格式

周文俊 , 蒋元旭 , 陈亮 , 刘开兴 , 余达刚 . 可见光与钯协同催化的有机合成化学[J]. 有机化学, 2020 , 40(11) : 3697 -3713 . DOI: 10.6023/cjoc202004045

Abstract

Palladium-catalyzed organic transformations is an important branch of organometallic chemistry. Because it can efficiently construct carbon-carbon bonds and carbon-heteroatom bonds, palladium catalysis has been widely used in synthetic chemistry, material science and pharmaceutical industry. However, some of these reactions suffer from harsh reaction conditions, including high temperature and strong base. On the other hand, the visible-light photoredox catalysis employs the visible light as the energy source to generate highly reactive intermediates and realize many novel transformations, which are rare under the normal thermal reaction conditions, under mild reaction conditions. However, there are also limitations in reaction types and substrate scope in this field. In order to solve such problems in these two fields, organic chemists have merged the visible-light photoredox catalysis and palladium catalysis, realizing a series of novel organic transformations through the electron transfer or energy transfer between photosensitizer and organic palladium complex under mild conditions with high efficiency and selectivity, which has broad substrate scope and great application potential. In these transformations, visible-light photoredox catalysis and palladium catalysis both play their respective roles and cooperate well. The application of visible light photoredox and palladium dual catalysis in organic synthesis is summarized and the future research directions in this field are analyzed, which might help the further development of this field.

Key words： visible-light photoredox catalysis; palladium catalysis; dual catalysis; organic synthesis

参考文献

[1] For select reviews:(a) Torborg, C.; Beller, M. Adv. Synth. Catal. 2009, 351, 3027.
(b) Knappke, C. E. I.; Jacobi von Wangelin, A. Chem. Soc. Rev. 2011, 40, 4948.
(c) Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912.
(d) Kambe, N.; Iwasaki, T.; Terao, J. Chem. Soc. Rev. 2011, 40, 4937.
(e) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107.
[2] For select reviews:(a) Liu, Q.; Dong, X.; Li, J.; Xiao, J.; Dong, Y.; Liu, H. ACS Catal. 2015, 5, 6111.
(b) Zhou, W.-J.; Zhang, Y.-H.; Cao, G.-M.; Liu, H.-D.; Yu, D.-G. Chin. J. Org. Chem. 2017, 37, 1322(in Chinese). (周文俊, 张逸寒, 曹光梅, 刘惠东, 余达刚, 有机化学, 2017, 37, 1322.)
[3] For select reviews:(a) Zeitler, K. Angew. Chem., Int. Ed. 2009, 48, 9785.
(b) Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527.
(c) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102.
(d) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322,
(e) Tan, F.; Xiao, W. Acta Chim. Sinica 2015, 73, 85(in Chinese). (谭芬, 肖文精, 化学学报, 2015, 73, 85.)
(f) Xuan, J.; Zhang, Z.-G.; Xiao, W.-J. Angew. Chem., Int. Ed. 2015, 54, 15632.
(g) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
(h) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2016, 45, 2044.
(i) Gui, Y.-Y.; Zhou, W.-J.; Ye, J.-H.; Yu, D.-G. ChemSusChem 2017, 10, 1337.
(j) Cheng, X.; Hu, X.; Lu, Z. Chin. J. Org. Chem. 2017, 37, 251(in Chinese). (程骁恺, 胡新根, 陆展, 有机化学, 2017, 37, 251.)
(k) Ding, K.; Xiao, W.; Wu, L. Acta Chim. Sinica 2017, 75, 5(in Chinese). (丁奎岭, 肖文精, 吴骊珠, 化学学报, 2017, 75, 5.)
(l) Pei, P.; Zhang, F.; Yi, H.; Lei, A. Acta Chim. Sinica 2017, 75, 15(in Chinese). (裴朋昆, 张凡, 易红, 雷爱文, 化学学报, 2017, 75, 15.)
(m) Wang, D.; Zhang, L.; Luo, S. Acta Chim. Sinica 2017, 75, 22(in Chinese). (王德红, 张龙, 罗三中, 化学学报, 2017, 75, 22.)
(n) Zhong, J.; Meng, Q.; Chen, B.; Tung, C.; Wu, L. Acta Chim. Sinica 2017, 75, 34(in Chinese). (钟建基, 孟庆元, 陈彬, 佟振合, 吴骊珠, 化学学报, 2017, 75, 34.)
(o) Zhang, J.; Chen, Y. Acta Chim. Sinica 2017, 75, 41(in Chinese). (张晶, 陈以昀, 化学学报, 2017, 75, 41.)
(p) Ye, H.; Xiao, C.; Lu, L. Chin. J. Org. Chem. 2018, 38, 1897(in Chinese). (叶辉, 肖聪, 陆良秋, 有机化学, 2018, 38, 1897.)
(q) Ruan, L.; Chen, C.; Zhang, X.; Sun, J. Chin. J. Org. Chem. 2018, 38, 3155(in Chinese). (阮利衡, 陈春欣, 张晓欣, 孙京, 有机化学, 2018, 38, 3155.)
(r) Wang, H.; Wu, P.; Zhao, X.; Zeng, J.; Wan, Q. Acta Chim. Sinica 2019, 77, 231(in Chinese). (王浩, 吴品儒, 赵祥, 曾静, 万谦, 化学学报, 2019, 77, 231.)
(s) Cai, B.-G.; Xuan, J.; Xiao, W.-J. Sci. Bull. 2019, 64, 337.
(t) Kong, Y.; Xu, W.; Ye, F.; Weng, J. Chin. J. Org. Chem. 2019, 39, 3065(in Chinese). (孔瑶蕾, 徐雯秀, 叶飞霞翁建全, 有机化学, 2019, 39, 3065.)
(u) Ren, L.; Ran, M.; He, J.; Qian, Y.; Yao, Q. Chin. J. Org. Chem. 2019, 39, 1583(in Chinese). (任林静, 冉茂刚, 何佳芯, 钱燕, 姚秋丽, 有机化学, 2019, 39, 1583.)
(v) Chen, J.; Li, Y.; Mei, L.; Wu, H. Chin. J. Org. Chem. 2019, 39, 3040(in Chinese). (陈锦杨, 李玉涵, 梅兰, 吴红谕, 有机化学, 2019, 39, 3040.)
(w) Chen, Y.; Lu, L.-Q.; Yu, D.-G.; Zhu, C.-J.; Xiao, W.-J. Sci. China:Chem. 2019, 62, 24.
(x) Hossain, A.; Bhattacharyya, A.; Reiser, O. Science 2019, 364, eaav9713.
(y) Li, S.; Xiang, S.-H.; Tan, B. Chin. J. Chem. 2020, 38, 213.
(z) Zhang, H.-H.; Chen, H.; Zhu, C.; Yu, S. Sci. China:Chem. 2020, 63, 637.
(aa) Yin, Y.; Zhao, X.; Qiao, B.; Jiang, Z. Org. Chem. Front. 2020, 7, 1283.
[4] For select reviews:(a) Paria, S.; Reiser, O. ChemCatChem 2014, 6, 2477.
(b) Hernandez-Perez, A. C.; Collins, S. K. Acc. Chem. Res. 2016, 49, 1557.
(c) Reiser, O. Acc. Chem. Res. 2016, 49, 1990.
(d) Parasram, M.; Gevorgyan, V. Chem. Soc. Rev. 2017, 46, 6227.
(e) Zhou, W.-J.; Cao, G.-M.; Zhang, Z.-P.; Yu, D.-G. Chem. Lett. 2019, 48, 181.
(f) Chuentragool, P.; Kurandina, D.; Gevorgyan, V. Angew. Chem., Int. Ed. 2019, 58, 11586. For select examples for visible light-excited Pd-catalysts, see:
(g) Kurandina, D.; Parasram, M.; Gevorgyan, V. Angew. Chem., Int. Ed. 2017, 56, 14212.
(h) Zhou, W.-J.; Cao, G.-M.; Shen, G.; Zhu, X.-Y.; Gui, Y.-Y.; Ye, J.-H.; Sun, L.; Liao, L.-L.; Li, J.; Yu, D.-G. Angew. Chem., Int. Ed. 2017, 56, 15683.
(i) Wang, G.-Z.; Shang, R.; Cheng, W.-M.; Fu, Y. J. Am. Chem. Soc. 2017, 139, 18307.
(j) Sun, L.; Ye, J.-H.; Zhou, W.-J.; Zeng, X.; Yu, D.-G. Org. Lett. 2018, 20, 3049.
(k) Zhou, Z.-Z.; Zhao, J.-H.; Gou, X.-Y.; Chen, X.-M.; Liang, Y.-M. Org. Chem. Front. 2019, 6, 1649.
(l) Sun, S.; Zhou, C.; Yu, J.-T.; Cheng, J. Org. Lett. 2019, 21, 6579.
(m) Kancherla, R.; Muralirajan, K.; Maity, B.; Zhu, C.; Krach, P. E.; Cavallo, L.; Rueping, M. Angew. Chem., Int. Ed. 2019, 58, 3412.
(n) Huang, H.-M.; Koy, M.; Serrano, E.; Pflüger, P. M.; Schwarz, J. L.; Glorius, F. Nat. Catal. 2020, 3, 393.
(o) Torres, G. M.; Liu, L.; Arndtsen, B. A. Science 2020, 368, 318.
[5] For select reviews:(a) Hopkinson, M. N.; Sahoo, B.; Li, J.-L.; Glorius, F. Chem.-Eur. J. 2014, 20, 3874.
(b) Gui, Y.-Y.; Sun, L.; Lu, Z.-P.; Yu, D.-G. Org. Chem. Front. 2016, 3, 522.
(c) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035.
(d) Levin, M. D.; Kim, S.; Toste, F. D. ACS Cent. Sci. 2016, 2, 293.
(e) Goddard, J.-P.; Ollivier, C.; Fensterbank, L. Acc. Chem. Res. 2016, 49, 1924.
(f) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035.
(g) Tóth, B. L.; Tischler, O.; Novák, Z. Tetrahedron Lett. 2016, 57, 4505.
(h) Tellis, J. C.; Kelly, C. B.; Primer, D. N.; Jouffroy, M.; Patel, N. R.; Molander, G. A. Acc. Chem. Res. 2016, 49, 1429.
(i) Hopkinson, M. N.; Tlahuext-Aca, A.; Glorius, F. Acc. Chem. Res. 2016, 49, 2261.
(j) Fabry, D. C.; Rueping, M. Acc. Chem. Res. 2016, 49, 1969.
(k) Lang, X.; Zhao, J.; Chen, X. Chem. Soc. Rev. 2016, 45, 3026.
(l) Zhou, W.-J.; Zhang, Y.-H.; Gui, Y.-Y.; Sun, L.; Yu, D.-G. Synthesis 2018, 50, 3359.
[6] Osawa, M.; Nagai, H.; Akita, M. Dalton. Trans. 2007, 2, 827.
[7] (a) Kalyani, D.; Mcmurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18566.
(b) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
[8] Neufeldt, S. R.; Sanford, M. S. Adv. Synth. Catal. 2012, 354, 3517.
[9] Liang, L.; Xie, M.-S.; Wang, H.-X.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. J. Org. Chem. 2017, 82, 5966.
[10] Khan, R.; Boonseng, S.; Kemmitt, P. D.; Felix, R.; Coles, J.; Tizzard, G. J.; Williams, G.; Simmonds, O.; Harvey, J.-L.; Atack, J.; Cox, H.; Spencer, J. Adv. Synth. Catal. 2017, 359, 3261.
[11] Jiang, J.; Zhang, W.-M.; Dai, J.-J.; Xu, J.; Xu, H.-J. J. Org. Chem. 2017, 82, 3622.
[12] Sahoo, M. K.; Midya, S. P.; Landge, G.; Balaraman, E. Green Chem. 2017, 19, 2111.
[13] Zhao, J.; Li, H.; Li, P.; Wang, L. J. Org. Chem. 2019, 84, 9007.
[14] Zhang, H.; Huang, X. Adv. Synth. Catal. 2016, 358, 3736.
[15] Czyz, M. L.; Lupton, D. W.; Polyzos, A. Chem.-Eur. J. 2017, 23, 14450.
[16] Xuan, J.; Zeng, T.-T.; Feng, Z.-J.; Deng, Q.-H.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J.; Alper, H. Angew. Chem., Int. Ed. 2015, 54, 1625.
[17] Lan g, S. B.; Nele, K. M. O.; Tunge, J. A. J. Am. Chem. Soc. 2014, 136, 13606.
[18] Lang, S. B.; Nele, K. M. O.; Douglas, J. T.; Tunge, J. A. Chem. Eur. J. 2015, 21, 18589.
[19] Zhang, H.-H.; Zhao, J.-J.; Yu, S. J. Am. Chem. Soc. 2018, 140, 16914.
[20] Zhang, H.-H.; Zhao, J.-J.; Yu, S. ACS Catal. 2020, 10, 4710.
[21] Zheng, C.; Cheng, W.; Li, H.; Na, R.; Shang, R. Org. Lett. 2018, 20, 2559.
[22] Shen, X.; Qian, L.; Yu, S. Sci. China:Chem. 2020, 63, 687.
[23] Liu, K.; Zou, M.; Lei, A. J. Org. Chem. 2016, 81, 7088.
[24] Zhou, C.; Li, P.; Zhu, X.; Wang, L. Org. Lett. 2015, 17, 6198.
[25] Xu, N.; Li, P.; Xie, Z.; Wang, L. Chem.-Eur. J. 2016, 22, 2236.
[26] Sharma, U. K.; Gemoets, H. P. L.; Schröder, F.; Noël, T.; Van der Eycken, E. V. ACS Catal. 2017, 7, 3818.
[27] Manna, M. K.; Bairy, G.; Jana, R. Org. Biomol. Chem. 2017, 15, 5899.
[28] Cheng, W.-M.; Shang, R.; Yu, H.-Z.; Fu, Y. Chem.-Eur. J. 2015, 21, 13191.
[29] Zhao, B.; Shang, R.; Cheng, W.; Fu, Y. Org. Chem. Front. 2018, 5, 1782.
[30] Shimomaki, K.; Murata, K.; Martin, R.; Iwasawa, N. J. Am. Chem. Soc. 2017, 139, 9467.
[31] Shimomaki, K.; Nakajima, T.; Caner, J.; Toriumi, N.; Iwasawa, N. Org. Lett. 2019, 21, 4486.
[32] Bhunia, S. K.; Das, P.; Nandi, S.; Jana, R. Org. Lett. 2019, 21, 4632.
[33] Zhu, C.; Zhang, Y.; Liu, Z.; Zhou, L.; Liu, H.; Feng, C. Chem. Sci. 2019, 10, 6721.
[34] Choi, S.; Chatterjee, T.; Choi, W. J.; You, Y.; Cho, E. J. ACS Catal. 2015, 5, 4796.
[35] Sheri, S.; Paul, A.; Bera, M.; Venkatesh, Y.; Singh, N. D. P. Org. Lett. 2018, 20, 5533.
[36] Zoller, J.; Fabry, D. C.; Ronge, M. A.; Rueping, M. Angew. Chem., Int. Ed. 2014, 53, 13264.
[37] Kato, S.; Saga, Y.; Kojima, M.; Fuse, H.; Matsunaga, S.; Fukatsu, A.; Kondo, M.; Masaoka, S.; Kanai, M. J. Am. Chem. Soc. 2017, 139, 2204.
[38] Under the revision of the manuscript, an elegant dehydrative allylation was reported, see:Masuda, Y.; Ito, M.; Mutakami, M. Org. Lett. 2020, 22,4467.
Options
文章导航

/

〈 〉