Review

Visible Light Induced Cross-Coupling Hydrogen Evolution Reactions

  • Zhong Jian-Ji ,
  • Meng Qing-Yuan ,
  • Chen Bin ,
  • Tung Chen-Ho ,
  • Wu Li-Zhu
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  • Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190

Received date: 2016-09-14

  Revised date: 2016-11-13

  Online published: 2016-11-24

Supported by

Project supported by the National Natural Science Foundation of China (Grant Nos. 21390404, 91427303, 21402217), the Ministry of Science and Technology of China (Grant Nos. 2013CB834804, 2013CB834505, 2014CB239402), the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB17030200).

Abstract

Taking advantages of the mild, clean and earth-abundant characters of visible light catalysis, we have invented a new reaction, namely cross-coupling hydrogen evolution (CCHE) reaction, for the construction of a series of C-C bond, C-X (heteroatom) bond, or X-X bond directly from two different C-H bonds, C-H and X-H bonds, or X-H and X-H bonds, respectively. In contrast to traditional strategies, this CCHE reaction avoids the use of any external oxidant and H2 is the sole product at ambient condition. In this contribution, we will highlight the development of CCHE reaction since the first report in 2013 to provide guidance for cleaner, safer, and more efficient, step-economic and atom-economic organic transformation.

Cite this article

Zhong Jian-Ji , Meng Qing-Yuan , Chen Bin , Tung Chen-Ho , Wu Li-Zhu . Visible Light Induced Cross-Coupling Hydrogen Evolution Reactions[J]. Acta Chimica Sinica, 2017 , 75(1) : 34 -40 . DOI: 10.6023/A16090491

References

[1] Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.
[2] Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393.
[3] Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
[4] Zhang, W.; Dai, J.; Xu, H. Chin. J. Org. Chem. 2015, 35, 1820 (in Chinese). (张文曼, 戴建军, 许华建, 有机化学, 2015, 35, 1820.)
[5] Yuan, D.; Zhang, Q.; Liao, S.; Xiong, W.; Yuan, L.; Cai, Q.; Yang, M.; Li, X.; Jiang, Y.; Liu, Y.; Li, P.; Xu, Z.; Sun, P.; Geng, H. Chin. J. Org. Chem. 2015, 35, 961 (in Chinese). (袁定重, 张庆华, 廖世军, 熊文文, 元利刚, 蔡奇胜, 杨梦梅, 李雄, 蒋烨佳, 刘妍, 李萍, 徐贞帅, 孙盼盼, 耿会玲, 有机化学, 2015, 35, 961.)
[6] Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013.
[7] Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
[8] Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
[9] Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
[10] Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
[11] Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293.
[12] Lu, Q.; Yi, H.; Lei, A. Acta Chim. Sinica 2015, 73, 1245 (in Chinese). (陆庆全, 易红, 雷爱文, 化学学报, 2015, 73, 1245.)
[13] Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
[14] Murahashi, S.-I.; Komiya, N.; Terai, H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312.
[15] Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
[16] Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
[17] Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem., Int. Ed. 2014, 53, 74.
[18] Ciamician, G. Science 1912, 36, 385.
[19] Nicewicz, D. A.; MacMillan, D. W. Science 2008, 322, 77.
[20] Zeitler, K. Angew. Chem., Int. Ed. 2009, 48, 9785.
[21] Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527.
[22] Narayanam, J. M.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102.
[23] Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[24] Xuan, J.; Zhang, Z.-G.; Xiao, W.-J. Angew. Chem., Int. Ed. 2015, 54, 15632.
[25] Ghosh, I.; Marzo, L.; Das, A.; Shaikh, R.; König, B. Acc. Chem. Res. 2016, 49, 1566.
[26] Zuo, X.; Wu, W.; Su, W. Acta Chim. Sinica 2015, 73, 1298 (in Chinese). (左璇, 吴文亮, 苏伟平, 化学学报, 2015, 73, 1298.)
[27] Lin, Q.; Chu, L.; Qing, F.-L. Chin. J. Chem. 2013, 31, 885.
[28] 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.
[29] Meng, Q.-Y.; Liu, Q.; Zhong, J.-J.; Zhang, H.-H.; Li, Z.-J.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2012, 14, 5992.
[30] 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.
[31] 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.
[32] 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.
[33] 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.
[34] 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, 4635.
[35] Zhang, G.; Liu, C.; Yi, H.; Meng, Q.; Bian, C.; Chen, H.; Jian, J.-X.; Wu, L.-Z.; Lei, A. J. Am. Chem. Soc. 2015, 137, 9273.
[36] Zhang, G.; Zhang, L.; Yi, H.; Luo, Y.; Qi, X.; Tung, C.-H.; Wu, L.-Z.; Lei, A. Chem. Commun. 2016, 52, 10407.
[37] Luo, K.; Chen, Y.-Z.; Yang, W.-C.; Zhu, J.; Wu, L. Org. Lett. 2016, 18, 452.
[38] Zhang, G.; Hu, X.; Chiang, C. W.; Yi, H.; Pei, P.; Singh, A. K.; Lei, A. J. Am. Chem. Soc. 2016, 138, 12037.
[39] 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.

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