可见光引发的氧自由基的新型产生方式及反应
收稿日期: 2016-08-15
修回日期: 2016-12-02
网络出版日期: 2017-01-13
基金资助
项目受国家重大科学研究计划项目（No.2014CB910304）、国家自然科学基金（Nos.21272260，21472230）和中国科学院战略性先导科技专项（B类）（No.XDB20020200）资助.
Visible-Light-Induced Carboxyl and Alkoxyl Radical Generations and Reactions
Received date: 2016-08-15
Revised date: 2016-12-02
Online published: 2017-01-13
Supported by
Project supported by the National Basic Research Program of China (No. 2014CB910304), National Natural Science Foundation of China (Nos. 21272260, 21472230) and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20020200).
张晶 , 陈以昀 . 可见光引发的氧自由基的新型产生方式及反应[J]. 化学学报, 2017 , 75(1) : 41 -48 . DOI: 10.6023/A16080416
The carboxyl and alkoxyl radicals generated from visible light photoredox reactions are important reaction intermediates in organic synthesis, which have witnessed conceivable progress recently. In this review, we focus on visible-light-induced photoredox methods to generate carboxyl radicals from carboxylate derivatives and carboxylates, as well as alkoxyl radicals from alcohol derivatives and alcohols, and briefly discuss their synthetic applications.
Key words： visible light; radical reaction; carboxyl radical; alkoxyl radical
[1] Gooßen, L. J.; Rodríguez, N.; Gooßen, K. Angew. Chem., Int. Ed. 2008, 47, 3100.
[2] Xuan, J.; Zhang, Z. G.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 15632.
[3] Huang, H.; Jia, K.; Chen, Y. ACS Catal. 2016, 6, 4983.
[4] Guan, B.; Xu, X.; Wang, H.; Li, X. Chin. J. Org. Chem. 2016, 36, 1564 (in Chinese). (关保川, 许孝良, 王红, 李小年, 有机化学, 2016, 36, 1564.)
[5] ?ekovi?, ?. Tetrahedron 2003, 59, 8073.
[6] Boto, A.; Hernandez, D.; Hernandez, R.; Suárez, E. J. Org. Chem. 2003, 68, 5310.
[7] Salamone, M.; Bietti, M. Acc. Chem. Res. 2015, 48, 2895.
[8] Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[9] Schultz, D. M.; Yoon, T. P. Science2014, 343, 985.
[10] Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102.
[11] Xuan, J.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 6828.
[12] Hu, C. C.; Chen, Y. Y. Tetrahedron Lett. 2015, 56, 884.
[13] Okada, K.; Okamoto, K.; Morita, N.; Okubo, K.; Oda, M. J. Am. Chem. Soc. 1991, 113, 9401.
[14] Schnermann, M. J.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9576.
[15] Yang, J.; Zhang, J.; Qi, L.; Hu, C. C.; Chen, Y. Y. Chem. Commun. 2015, 51, 5275.
[16] Hu, C. C.; Chen, Y. Y. Org. Chem. Front. 2015, 2, 1352.
[17] Xie, J.; Xu, P.; Li, H. M.; Xue, Q. C.; Jin, H. M.; Cheng, Y. X.; Zhu, C. J. Chem. Commun. 2013, 49, 5672.
[18] He, Z.; Bae, M.; Wu, J.; Jamison, T. F. Angew. Chem., Int. Ed. 2014, 53, 14451.
[19] Kachkovskyi, G.; Faderl, C.; Reiser, O. Adv. Synth. Catal. 2013, 355, 2240.
[20] Zuo, Z. W.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257.
[21] Ventre, S.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654.
[22] Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R. P.; Qi, X. T.; Lan, Y.; Lei, A. W. Angew. Chem., Int. Ed. 2014, 53, 502.
[23] Chu, L. L.; Lipshultz, J. M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 7929.
[24] Wang, G. Z.; Shang, R.; Cheng, W. M.; Fu, Y. Org. Lett. 2015, 17, 4830.
[25] Zhou, Q. Q.; Guo, W.; Ding, W.; Wu, X.; Chen, X.; Lu, L. Q.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 11196.
[26] Le Vaillant, F.; Courant, T.; Waser, J. Angew. Chem., Int. Ed. 2015, 54, 11200.
[27] Wu, X. X.; Meng, C. N.; Yuan, X. Q.; Jia, X. T.; Qian, X. H.; Ye, J. X. Chem. Commun. 2015, 51, 11864.
[28] Luo, J.; Zhang, J. ACS Catal.2016, 6, 873.
[29] Huang, H. C.; Zhang, G. J.; Chen, Y. Y. Angew. Chem., Int. Ed. 2015, 54, 7872.
[30] Tan, H.; Li, H. J.; Ji, W. Q.; Wang, L. Angew. Chem. Int. Ed. 2015, 54, 8374.
[31] Zhang, J.; Li, Y.; Zhang, F. Y.; Hu, C. C.; Chen, Y. Y. Angew. Chem., Int. Ed. 2016, 55, 1872.
[32] Wang, C. Y.; Harms, K.; Meggers, E. Angew. Chem., Int. Ed. 2016, 55, 13495.
[33] Jia, K. F.; Zhang, F. Y.; Huang, H. C.; Chen, Y. Y. J. Am. Chem. Soc. 2016, 138, 1514.
[34] Yayla, H. G.; Wang, H. J.; Tarantino, K. T.; Orbe, H. S.; Knowles, R. R. J. Am. Chem. Soc. 2016, 138, 10794.
[35] Guo, J. J.; Hu, A. H.; Chen, Y. L.; Sun, J. F.; Tang, H. M.; Zuo, Z. W. Angew. Chem., Int. Ed. 2016, 55, 15319.
[36] Hu, X. Q.; Chen, J.; Chen, J. R.; Yan, D. M.; Xiao, W. J. Chem. Eur. J. 2016, 22, 14141.
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