Cross-Coupling Hydrogen Evolution Reactions

doi:10.6023/A19110412

Acta Chimica Sinica ›› 2020, Vol. 78 ›› Issue (4): 299-310.DOI: 10.6023/A19110412 Previous Articles Next Articles

Review

放氢交叉偶联反应

董奎^a, 刘强^a, 吴骊珠^a,b

a 兰州大学功能有机分子化学国家重点实验室兰州 730000;
b 中国科学院理化技术研究所光化学转换与功能材料重点实验室北京 100190

投稿日期:2019-11-23 发布日期:2020-03-12
通讯作者: 刘强, 吴骊珠 E-mail:liuqiang@lzu.edu.cn;lzwu@mail.ipc.ac.cn
作者简介:董奎,1994年出生于江苏淮安,2017年毕业于兰州大学,获学士学位.目前在刘强教授指导下攻读博士学位.研究兴趣为酚类化合物偶联反应;刘强,2001年和2006年分别在兰州大学获得学士和博士学位.毕业后留校工作,历任讲师、副教授、教授.2009年到2011年在中国科学院理化技术研究所超分子光化学研究组从事博士后研究.现为兰州大学功能有机分子化学国家重点实验室教授,博士生导师,中国化学会光化学专业委员会委员.主要研究领域涉及有机光化学和自由基合成化学;吴骊珠,1990年毕业于兰州大学化学系,获学士学位.1995年毕业于中国科学院感光化学研究所,获博士学位.毕业后留所工作,历任助理研究员、副研究员、研究员.1997年至1998年赴香港大学化学系从事博士后研究.现为中国科学院理化技术研究所研究员,博士生导师.长期致力于光化学研究,涉及太阳能光化学转换、光化学合成与技术、超分子体系中重要的光物理和光化学过程.曾获国家自然科学基金杰出青年基金资助(2001)、国家自然科学二等奖(2005,第二完成人)、中国青年科技奖(2007)、中国青年女科学家奖(2010)、中国化学会-物理有机化学奖(2013)、中国化学会-赢创化学创新奖(2016)、国家万人计划百千万工程领军人才(2016).2019年当选中国科学院院士.
基金资助:
项目受国家自然科学基金（Nos.21572090，91427303，21402217，21390404）、科技部（Nos.2013CB834804，2013CB834505，2014CB239402）和中国科学院战略性先导科技专项（B类）（No.XDB17030200）资助.

Cross-Coupling Hydrogen Evolution Reactions

Dong Kui^a, Liu Qiang^a, Wu Li-Zhu^a,b

a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000;
b Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190

Received:2019-11-23 Published:2020-03-12
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572090, 91427303, 21402217, 21390404), the Ministry of Science and Technology of China (Nos. 2013CB834804, 2013CB834505, 2014CB239402) and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB17030200).

During the past decade, transition metal-catalyzed dehydrogenative cross-couplings have emerged as an attractive strategy in synthetic chemistry due to its high step- and atom-economy as well as the less functionalized coupling partners. However, such reactions have to always use stoichiometric amount of sacrificial oxidants such as peroxides, high-valent metals (Cu salts, Ag salts, etc.), or iodine(III) oxidants, thereby leading to possible generation of toxic wastes and making the process less desirable from a green chemistry perspective. The recently developed photocatalytic CCHE (cross-coupling hydrogen-evolution) reactions are a conceptually new type of reactions enabled by combination of photo-redox catalysis and proton reduction catalysis, wherein the photocatalyst uses light energy as the driving force for the cross-coupling and the hydrogen evolution catalyst may capture electrons and protons from the substrates or reaction intermediates to produce molecular hydrogen (H₂). Thus, without use of any sacrificial oxidant and under mild conditions, the dual catalyst system may afford cross-coupling products with excellent yields and an equivalent amount of H₂ as the sole byproduct. This kind of cross-coupling delivers a greener synthetic strategy and is particularly useful for reactions that involve species sensitive to traditional oxidants. In CCHE reactions, the raw materials are directly converted into products and hydrogen, the reactions are highly atom economy, environmentally friendly, and have attractive potential industrial application prospects. In this review, recent dramatic developments of photocatalytic and electrochemical CCHE reactions are discussed via the most prominent mechanistic pathways, the types of C-C bond, C-X (heteroatom) bond, or X-X bond formations and specific reaction classes.

Key words: cross-coupling hydrogen evolution, visible-light photocatalysis, electrosynthesis, green chemistry, synthetic strategy

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Dong Kui, Liu Qiang, Wu Li-Zhu. Cross-Coupling Hydrogen Evolution Reactions[J]. Acta Chimica Sinica, 2020, 78(4): 299-310.

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[1] Zhong, J.-J.; Meng, Q.-Y.; Chen, B.; Tung, C.-H.; Wu, L.-Z. 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).
[2] Liu, Q.; Wu, L.-Z. Natl. Sci. Rev. 2017, 4, 359.
[3] Chen, B.; Wu, L.-Z.; Tung, C.-H. Acc. Chem. Res. 2018, 51, 2512.
[4] Meng, Q.-Y.; Zhong, J.-J.; Liu, Q.; Gao, X.-W.; Zhang, H.-H.; Lei, T.; Li, Z.-J.; Feng, K.; Chen, B.; Tung, C.-H.; Wu, L.-Z. J. Am. Chem. Soc. 2013, 135, 19052.
[5] Zhong, J.-J.; Meng, Q.-Y.; Liu, B.; Li, X.-B.; Gao, X.-W.; Lei, T.; Wu, C.-J.; Li, Z.-J.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2014, 16, 1988.
[6] Gao, X.-W.; Meng, Q.-Y.; Li, J.-X.; Zhong, J.-J.; Lei, T.; Li, X.-B.; Tung, C.-H.; Wu, L.-Z. ACS Catal. 2015, 5, 2391.
[7] Xiang, M.; Meng, Q.-Y.; Li, J.-X.; Zheng, Y.-W.; Ye, C.; Li, Z.-J.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Chem. Eur. J. 2015, 21, 18080.
[8] Cao, W. X.; Wu, C. J.; Lei, T.; Yang, X. L.; Chen, B.; Tung, C. H.; Wu, L. Z. Chin. J. Catal. 2018, 39, 1194.
[9] Tang, S.; Zeng, L.; Lei, A. W. J. Am. Chem. Soc. 2018, 140, 13128.
[10] Wang, H. M.; Gao, X. L.; Lv, Z. C.; Abdelilah, T.; Lei, A. W. Chem. Rev. 2019, 119, 6769.
[11] Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.; Evans, R. W.; MacMillan, D. W. C. Nat. Rev. Chem. 2017, 1, 0052.
[12] Tyagi, A.; Yamamoto, A.; Yamamoto, M.; Yoshidad, T.; Yoshida, H. Catal. Sci. Technol. 2018, 8, 2546.
[13] Girish, Y. R.; Jaiswal, K.; Prakash, P.; De, M. Catal. Sci. Technol. 2019, 9, 1201.
[14] Wu, C. J.; Meng, Q. Y.; Lei, T.; Zhong, J. J.; Liu, W. Q.; Zhao, L. M.; Li, Z. J.; Chen, B.; Tung, C. H.; Wu, L. Z. ACS Catal. 2016, 6, 4635.
[15] Hu, X.; Zhang, G. T; Bu, F. X.; Luo, X.; Yi, K. B.; Zhang, H.; Lei, A. W. Chem. Sci. 2018, 9, 1521.
[16] Zhang, G. T.; Lin, Y. L.; Luo, X.; Hu, X.; Chen, C.; Lei, A. W. Nat. Commun. 2018, 9, 1225.
[17] Lin, J.; Li, Z.; Kan, J.; Huang, S. J.; Su, W. P.; Li, Y. D. Nat. Commun. 2017, 8, 14353.
[18] Cao, H.; Jiang, H. M.; Feng, H. Y.; Kwan, J. M. C.; Liu, X. G.; Wu, J. J. Am. Chem. Soc. 2018, 140, 16360.
[19] Sun, X.; Chen, J.; Ritter, T. Nature Chem. 2018, 10, 1229.
[20] Nguyen, V. T.; Nguyen, V. D.; Haug, G. C.; Dang, H. T.; Jin, S.; Li, Z.; Flores-Hansen, C.; Benavides, B. S.; Arman, H. D.; Larionov, O. V. ACS Catal. 2019, 9, 9485.
[21] Kirste, A.; Elsler, B.; Schnakenburg, G.; Waldvogel, S. R. J. Am. Chem. Soc. 2012, 134, 3571.
[22] Elsler, B.; Schollmeyer, D.; Dyballa, K. M.; Franke, R.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2014, 53, 5210.
[23] Wiebe, A.; Lips, S.; Schollmeyer, D.; Franke, R.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2017, 56, 14727.
[24] Lips, S.; Schollmeyer, D.; Franke, R.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2018, 57, 13325.
[25] Schulz, L.; Enders, M.; Elsler, B.; Schollmeyer, D.; Dyballa, K. M.; Franke, R.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2017, 56, 4877.
[26] Wu, Z. J.; Xu, H. C. Angew. Chem., Int. Ed. 2017, 56, 4734.
[27] Zhang, G. T.; Hu, X.; Chiang, C. W.; Yi, H.; Pei, P. K.; Singh, A. K.; Lei, A. W. J. Am. Chem. Soc. 2016, 138, 12037.
[28] Yi, H.; Niu, L.; Song, C.; Li, Y.; Dou, B.; Singh, A. K.; Lei, A. W. Angew. Chem., Int. Ed. 2017, 56, 1120.
[29] Zhang, M.; Ruzi, R.; Li, N.; Xie, J.; Zhu, C. J. Org. Chem. Front. 2018, 5, 749.
[30] Shao, A.; Li, N.; Gao, Y.; Zhan, J.; Chiang, C.-W.; Lei, A. W. Chin. J. Chem. 2018, 36, 619.
[31] Shao, A.; Zhan, J.; Li, N.; Chiang, C.-W.; Lei, A. W. J. Org. Chem. 2018, 83, 3582.
[32] Yang, Q.; Jia, Z. B.; Li, L. J.; Zhang, L.; Luo, S. Z. Org. Chem. Front. 2018, 5, 237.
[33] Hu, X.; Zhang, G.; Bu, F.; Lei, A. W. Angew. Chem., Int. Ed. 2018, 57, 1286.
[34] Tian, W.-F.; Wang, D.-P.; Wang, S.-F.; He, K.-H.; Cao, X.-P.; Li, Y. Org. Lett. 2018, 20, 1421.
[35] Niu, L.; Yi, H.; Wang, S.; Liu, T.; Liu, J.; Lei, A. W. Nat. Commun. 2017, 8, 14226.
[36] Chen, H.; Yi, H.; Tang, Z. L.; Bian, C. L.; Zhang, H.; Lei, A. W. Adv. Synth. Catal. 2018, 360, 3220.
[37] Zhao, F. Q.; Yang, Q.; Zhang, J. J.; Shi, W. M.; Hu, H. H.; Liang, F.; Wei, W.; Zhou, S. L. Org. Lett. 2018, 20, 7753.
[38] Zhao, Q.-Q.; Hu, X.-Q.; Yang, M.-N.; Chen, J.-R.; Xiao, W.-J. Chem. Commun. 2016, 52, 12749.
[39] Zhong, J.-J.; To, W.-P.; Liu, Y.; Lu, W.; Che, C.-M. Chem. Sci. 2019, 10, 4883.
[40] Tang, S.; Wang, S. Y.; Liu, Y. C.; Cong, H. J.; Lei, A. W. Angew. Chem., Int. Ed. 2018, 57, 4737.
[41] Wang, J. H.; Lei, T.; Nan, X. L.; Wu, H. L.; Li, X. B.; Chen, B.; Tung, C. H.; Wu, L. Z. Org. Lett. 2019, 21, 5581.
[42] Sauermann, N.; Mei, R.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 5090.
[43] Gao, X. L.; Wang, P.; Zeng, L.; Tang, S.; Lei, A. W. J. Am. Chem. Soc. 2018, 140, 4195.
[44] Yang, Q. L.; Wang, X. Y.; Lu, J. Y.; Zhang, L. P.; Fang, P.; Mei, T. S. J. Am. Chem. Soc. 2018, 140, 11487.
[45] Zhao, H.-B.; Hou, Z.-W.; Liu, Z.-J.; Zhou, Z.-F.; Song, J.-S.; Xu, H.-C. Angew. Chem., Int. Ed. 2017, 56, 587.
[46] Niu, L. B.; Wang, S. C.; Liu, J. M.; Yi, H.; Liang, X. A.; Liu, T. Y.; Lei, A. W. Chem. Commun. 2018, 54, 1659.
[47] Luo, K.; Chen, Y.-Z.; Yang, W.-C.; Zhu, J.; Wu, L. Org. Lett. 2016, 18, 452.
[48] Liu, W. Q.; Lei, T.; Zhou, S.; Yang, X. L.; Li, J.; Chen, B.; Sivaguru, J.; Tung, C. H.; Wu, L. Z. J. Am. Chem. Soc. 2019, 141, 13941.
[49] Wang, J. H.; Li, X. B.; Li, J.; Lei, T.; Wu, H. L.; Nan, X. L.; Tung, C. H.; Wu, L. Z. Chem. Commun. 2019, 55, 10376.
[50] Zhang, G.; Liu, C.; Yi, H.; Meng, Q.; Bian, C.; Chen, H.; Jian, J.-X.; Wu, L.-Z.; Lei, A. W. J. Am. Chem. Soc. 2015, 137, 9273.
[51] Zhang, G.; Zhang, L.; Yi, H.; Luo, Y.; Qi, X.; Tung, C.-H.; Wu, L.-Z.; Lei, A. W. Chem. Commun. 2016, 52, 10407.
[52] Wang, P.; Tang, S.; Huang, P. F.; Lei, A. W. Angew. Chem., Int. Ed. 2017, 56, 3009.
[53] Yuan, Y.; Cao, Y.; Qiao, J.; Lin, Y.; Jiang, X.; Weng, Y.; Tang, S.; Lei, A. W. Chin. J. Chem. 2019, 37, 49.
[54] Liu, W.-Q.; Yang, X.-L.; Tung, C.-H.; Wu, L.-Z. Acta Chim. Sinica 2019, 77, 861(in Chinese). (刘文强, 杨修龙, 佟振合, 吴骊珠, 化学学报, 2019, 77, 861).
[55] Lu, F.-L.; Yang, Z.-Z.; Wang, T.; Wang, T.-H.; Zhang, Y.-Y.; Yuan, Y.; Lei, A.-W. Chin. J. Chem. 2019, 37, 547.
[56] Yu, W. L.; Luo, Y. C.; Yan, L.; Liu, D.; Wang, Z. Y.; Xu, P. F. Angew. Chem., Int. Ed. 2019, 58, 10941.
[57] Li, X.-B.; Li, Z.-J.; Gao, Y.-J.; Meng, Q.-Y.; Yu, S.; Weiss, R. G.; Tung, C.-H.; Wu, L.-Z. Angew. Chem., Int. Ed. 2014, 53, 2085.
[58] He, K.-H.; Tan, F.-F.; Zhou, C.-Z.; Zhou, G.-J.; Yang, X.-L.; Li, Y. Angew. Chem., Int. Ed. 2017, 56, 3080.
[59] 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.
[60] Yin, Q.; Oestreich, M. Angew. Chem., Int. Ed. 2017, 56, 7716.
[61] Chai, Z. G.; Zeng, T. T.; Li, Q.; Lu, L. Q.; Xiao, W. J.; Xu, D. S. J. Am. Chem. Soc. 2016, 138, 10128.
[62] Zhao, L.-M.; Meng, Q.-Y.; Fan, X.-B.; Ye, C.; Li, X.-B.; Chen, B.; Ramamurthy, V.; Tung, C.-H.; Wu, L.-Z. Angew. Chem., Int. Ed. 2017, 56, 3020.
[63] Huang, C.; Li, X.-B.; Tung, C.-H.; Wu, L.-Z. Chem. Eur. J. 2018, 24, 11530.
[64] Yang, X.-J.; Zheng, Y.-W.; Zheng, L.-Q.; Wu, L.-Z.; Tung, C.-H.; Chen, B. Green Chem. 2019, 21, 1401.
[65] Sahoo, M. K.; Saravanakumar, K.; Jaiswal, G.; Balaraman, E. ACS Catal. 2018, 8, 7727.
[66] West, J. G.; Huang, D.; Sorensen, E. J. Nat. Commun. 2015, 6, 10093.
[67] Zhong, J.-J.; Wu, C.-J.; Meng, Q.-Y.; Gao, X.-W.; Lei, T.; Tung, C.-H.; Wu, L.-Z. Adv. Synth. Catal. 2014, 356, 2846.
[68] Yang, X. L.; Guo, J. D.; Lei, T.; Chen, B.; Tung, C. H.; Wu, L. Z. Org. Lett. 2018, 20, 2916.
[69] Yang, Q.; Zhang, L.; Ye, C.; Luo, S. Z.; Wu, L.-Z.; Tung, C.-H. Angew. Chem., Int. Ed. 2017, 56, 3694.
[70] Zheng, Y.-W.; Chen, B.; Ye, P.; Feng, K.; Wang, W.; Meng, Q.-Y.; Wu, L.-Z.; Tung, C.-H. J. Am. Chem. Soc. 2016, 138, 10080.
[71] Zheng, Y.-W.; Ye, P.; Chen, B.; Meng, Q.-Y.; Feng, K.; Wang, W.; Wu, L.-Z.; Tung, C.-H. Org. Lett. 2017, 19, 2206.
[72] Su, X. J. Am. Chem. Soc. 2013, 135, 19047.
[73] Su, X. J. Am. Chem. Soc. 2016, 138, 11409.
[74] Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97.
[75] Yi, H.; Niu, L. B.; Song, C. L.; Li, Y. Y.; Dou, B. W.; Singh, A. K.; Lei, A. W. Angew. Chem. 2017, 129, 1140.
[76] Tang, S.; Gao, X. L.; Lei, A. W. Chem. Commun. 2017, 53, 3354.
[77] He, K.-H.; Li, Y. ChemSusChem 2014, 7, 2788.
[78] Li, W.-H.; Wu, L.; Li, S.-S.; Liu, C.-F.; Zhang, G.-T.; Dong, L. Chem. Eur. J. 2016, 22, 17926.
[79] Chen, C.; Chen, X.; Zhao, H.; Jiang, H.; Zhang, M. Org. Lett. 2017, 19, 3390.
[80] Ren, L.-J.; Ran, M.-G.; He, J.-X.; Qian, Y.; Yao, Q.-L. 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).

放氢交叉偶联反应

Cross-Coupling Hydrogen Evolution Reactions

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