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).
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
Zhang Jing , Chen Yiyun . Visible-Light-Induced Carboxyl and Alkoxyl Radical Generations and Reactions[J]. Acta Chimica Sinica, 2017 , 75(1) : 41 -48 . DOI: 10.6023/A16080416
[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.
/
〈 |
|
〉 |