醛基为受体的氧化自由基加成反应研究进展
收稿日期: 2018-05-31
修回日期: 2018-06-27
网络出版日期: 2018-07-24
基金资助
国家自然科学基金（No.21672191）资助项目.
Recent Advances on Oxidative Radical Addition to Aldehydes
Received date: 2018-05-31
Revised date: 2018-06-27
Online published: 2018-07-24
Supported by
Project supported by the National Natural Science Foundation of China (No. 21672191).
孔黎春 , 周雨露 , 罗芳 , 朱钢国 . 醛基为受体的氧化自由基加成反应研究进展[J]. 有机化学, 2018 , 38(11) : 2858 -2865 . DOI: 10.6023/cjoc201805061
Ketones are ubiquitous chemical entries in natural products, biologically active molecules, and functional materials. As such, developing operationally simple and general methods for the synthesis of these scaffolds is highly desiable. Recently, oxidative radical addition to aldehydes has emerged as a highly efficient strategy for the direct access of ketones. The strategy features a formal 1,2-hydrogen atom transfer of resulting alkoxy radicals, followed by single electron transfer oxidation and deprotonation to give various cyclic or acyclic ketones in promising yields with a broad substrate scope. Recent advances in this area, including both intramolecular and intermolecular versions, are discussed herein.
[1] (a) Liu, C.; Liu, D.; Lei, A. Acc. Chem. Res. 2014, 47, 3459.
(b) Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598.
(c) Song, R.-J.; Liu, Y.; Xie, Y.-X.; Li, J.-H. Synthesis 2015, 47, 1195.
(d) Chen, J.-R.; Yu, X.-Y.; Xiao, W.-J. Synthesis 2015, 47, 604.
(e) Yin, G.; Mu, X.; Liu, G. Acc. Chem. Res. 2016, 49, 2413.
(f) 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.)
(g) Song, H.; Liu, X.; Qin, Y. Acta Chim. Sinica 2017, 75, 1137(in Chinese). (宋颢, 刘小宇, 秦勇, 化学学报, 2017, 75, 1137.)
(h) Zhao, J.; Duan, X.; Guo, L.-N. Chin. J. Org. Chem. 2017, 37, 2498(in Chinese). (赵景峰, 段新华, 郭丽娜, 有机化学, 2017, 37, 2498.)
(i) Rong, J.; Ni, C.; Wang, Y.; Kuang, C.; Gu, Y.; Hu, J. Acta Chim. Sinica 2017, 75, 105(in Chinese). (荣健, 倪传法, 王云泽, 匡翠文, 顾玉诚, 胡金波, 化学学报, 2017, 75, 105.)
(j) Yuan, S.; Wang, Y.; Qiu, G.; Liu, J. Chin. J. Org. Chem. 2017, 37, 566(in Chinese). (袁斯甜, 王艳华, 邱观音生, 刘晋彪, 有机化学, 2017, 37, 566.)
[2] (a) Miyabe, H.; Ueda, M.; Naito, T. Synlett 2004, 7, 1140.
(b) Xu, P.; Wang, G.; Zhu, Y.; Li, W.; Cheng, Y.; Li, S.; Zhu, C. Angew. Chem., Int. Ed. 2016, 55, 2939.
[3] (a) Wilsey, S.; Dowd, P.; Houk, K. N. J. Org. Chem. 1999, 64, 8801.
(b) Zhang, J.; Chen, Y. Acta Chim. Sinica 2017, 75, 41(in Chinese). (张晶, 陈以昀, 化学学报, 2017, 75, 41.)
[4] (a) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 111, 2674.
(b) Chang, S.-Y.; Shao, Y.-F.; Chu, S.-F.; Fan, G.-T.; Tsai, Y.-M. Org. Lett. 1999, 1, 945.
[5] Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116.
[6] Kawamoto, T.; Fukuyama, T.; Ryu, I. J. Am. Chem. Soc. 2012, 134, 875.
[7] Pitzer, L.; Sandfort, F.; Strieth-Kalthoff, F.; Glorius, F. J. Am. Chem. Soc. 2017, 139, 13652.
[8] Wang, G.; Cao, J.; Gao, L.; Chen, W.; Huang, W.; Cheng, X.; Li, S. J. Am. Chem. Soc. 2017, 139, 3904.
[9] (a) Gilbert, B. C.; Holmes, R. G. G.; Laue, H. A. H.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1976, 1047.
(b) Konya, K. G.; Paul, T.; Lin, S.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 2000, 122, 7518.
[10] Che, C.; Huang, Q.; Zheng, H.; Zhu, G. Chem. Sci. 2016, 7, 4134.
[11] Zhang, Y.; Guo, D.; Ye, S.; Liu, Z.; Zhu, G. Org. Lett. 2017, 19, 1302.
[12] (a) Muller, C. K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(c) Chen, P.; Liu, G. Synthesis 2013, 45, 2919.
(d) Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513.
(e) Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598.
(f) Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765.
(g) Nie, X.; Cheng, C.; Zhu, G. Angew. Chem., Int. Ed. 2017, 56, 1898.
[13] Zhang, Y.; Ye, S.; Ji, M.; Li, L.; Guo, D.; Zhu, G. J. Org. Chem. 2017, 82, 6811.
[14] Zhu, H.; Nie, X.; Huang, Q.; Zhu G. Tetrahedron Lett. 2016, 57, 2331.
[15] Lu, D.; Wan, Y.; Kong, L.; Zhu, G. Org. Lett. 2017, 19, 2929.
[16] Liu, Z.; Bai, Y.; Zhang, J.; Yu, Y.; Tan, Z.; Zhu, G. Chem. Commun. 2017, 53, 6440.
[17] Chen, Y.; Shu, C.; Luo, F.; Xiao, X.; Zhu, G. Chem. Commun. 2018, 54, 5373.
[18] Yang, W.-C.; Dai, P.; Luo, K.; Ji, Y.-G.; Wu, L. Adv. Synth. Catal. 2017, 359, 2390.
[19] (a) Zhao, H.; Fan, X.; Yu, J.; Zhu, C. J. Am. Chem. Soc. 2015, 137, 3490.
(b) Fan, X.; Zhao, H.; Yu, J.; Bao, X.; Zhu, C. Org. Chem. Front. 2016, 3, 227.
(c) Wang, S.; Guo, L.-N.; Wang, H.; Duan, X.-H. Org. Lett. 2015, 17, 4798.
(d) Jia, K.; Zhang, F.; Huang, H.; Chen, Y. J. Am. Chem. Soc. 2016, 138, 1514.
(e) Ilangovan, A.; Saravanakumar, S.; Malayappasamy, S. Org. Lett. 2013, 15, 4968.
[20] Che, C.; Qian, Z.; Wu, M.; Zhao, Y.; Zhu, G. J. Org. Chem. 2018, 83, 5665.
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