Chinese Journal of Organic Chemistry >
Study on the α-Acetoxylation of sp3-C-H Bonds Adjacent to Carbonyl of Arones
Received date: 2015-10-12
Revised date: 2015-11-21
Online published: 2015-12-10
Supported by
Project supported by the Outstanding Youth Fund of Guangdong Province (No. 2013LYM_0059).
In this work, an efficient α-acetoxylation of sp3-C-H bonds adjacent to carbonyl of arones to construct α-acetoxy acetophenone derivatives was developed. The influences of reaction time, copper salts, iodine and the loading of copper salts and iodine on this transformation were investigated, and the optimal reaction conditions were also obtained. In addition, a possible reaction mechanism was proposed. This protocol with its advantages of simple procedure and high yield provides a novel valuable approach to α-acetoxy acetophenones.
Key words： acetophenone; sp3-C-H bond; acetoxylation; α-acetoxy acetophenone
Chen Cui , Qiu Huihua . Study on the α-Acetoxylation of sp3-C-H Bonds Adjacent to Carbonyl of Arones[J]. Chinese Journal of Organic Chemistry, 2016 , 36(4) : 826 -829 . DOI: 10.6023/cjoc201510011
[1] Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193.
[2] Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177
[3] Zhu, C.; Yang, B.; Bäckvall, J. E. J. Am. Chem. Soc. 2015, 137, 11868.
[4] Henrion, M.; Ritleng, V.; Chetcuti, M. J. ACS Catal. 2015, 5, 1283.
[5] Zhang, Y.; Feng, B. N. Chin. J. Org. Chem. 2014, 34, 2406 (in Chinese). (张艳, 冯柏年, 有机化学, 2014, 34, 2406.)
[6] Chen, T. B.; Zhang, M. Chin. J. Org. Chem. 2015, 35, 813 (in Chinese). (陈天保, 章明, 有机化学, 2015, 35, 813.)
[7] Ni, C. F.; Zhu, L. G.; Hu, J. B. Acta Chim. Sinica 2015, 73, 90 (in Chinese). (倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.)
[8] Liu, J.; Zhu, Q. R.; Du, J. A.; Zhang, X. L. Chin. J. Org. Chem. 2015, 35, 15 (in Chinese). (刘杰, 朱庆仁, 杜娟, 张袖丽, 有机化学, 2015, 35, 15.)
[9] Gang, F. L.; Xu, G. L.; Dong, T. S.; Yang, L.; Du, Z. Y. Chin. J. Org. Chem. 2015, 35, 1428 (in Chinese). (刚芳莉, 徐光利, 董涛生, 杨丽, 杜正银, 有机化学, 2015, 35, 1428.)
[10] Wu, J. L.; Xiang, H. H.; Zeng, J.; Leow, M. L.; Liu, X. W. Org. Lett. 2015, 17, 222.
[11] Gurram, V.; Akula, H. K.; Garlapati1, R.; Pottabathini, N.; Lakshman, M. K. Adv. Synth. Catal. 2015, 357, 451.
[12] Tang, C. H.; Jiao, N. Angew. Chem., Int. Ed. 2014, 53, 6528.
[13] Greenhalgh, M. D.; Frank, D. J.; Thomas, S. P. Angew. Chem., Int. Ed. 2014, 356, 584.
[14] Green, R. A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2015, 54, 3768.
[15] Reid, E. B.; Fortenbauch, R. B.; Patterson, H. R. J. Org. Chem. 1950, 15, 579.
[16] Shindo, M.; Yoshimura, Y.; Hayashi, M.; Soejima, H.; Yoshikawa, T.; Matsumoto, K.; Shishido, K. Org. Lett. 2007, 9, 1963.
[17] Lee, J. C.; Jin, Y. S.; Choi, J. H. Chem. Commun. 2001, 956.
[18] Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. J. Am. Chem. Soc. 2005, 127, 12244.
[19] Demir, A. S.; Hamamci, H.; Tanyeli, C.; Akhmedov, I. M.; Doganel, F. Tetrahedron: Asymmetry 1998, 9, 1673.
[20] Sheng, J. M.; Li, X. L.; Tang, M. F.; Gao, B. T.; Huang, G. S. Synthesis 2007, 1165.
[21] Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2011, 50, 5331.
[22] Cort, A. D. J. Org. Chem. 1991, 56, 6708.
[23] Yin, G. D.; Gao, M.; She, N. F.; Hu, S. L.; Wu, A. X.; Pan, Y. J. Synthesis 2007, 3113.
[24] Wang, Z. H.; Yin, G. D.; Qin, J.; Gao, M.; Cao, L. P.; Wu, A. X. Synthesis 2008, 3675.
[25] Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2011, 50, 5331.
[26] Anastasaki, A.; Nikolaou, V.; Zhang, Q.; Burns, J.; Samanta, S. R.; Waldron, C.; Haddleton, A. J.; McHale, R.; Fox, D.; Percec, V.; Wilson, P.; Haddleton, D. M. J. Am. Chem. Soc. 2014, 136, 1141.
[27] Tan, L. Q.; Liu, W. B.; Huang, M.; Yu, M. Chin. J. Org. Chem. 2014, 34, 817 (in Chinese). (谭丽泉, 刘卫兵, 黄敏, 于梅, 有机化学, 2014, 34, 817.)
[28] Percec, V.; Guliashvili, T.; Ladislaw, J. S.; Wistrand, A.; Stjerndahl, A.; Sienkowska, M. J.; Monteiro, M. J.; Sahoo, S. J. Am. Chem. Soc. 2006, 128, 14156.
[29] Walker, E. H.; Apblett, A. W.; Walker, R.; Zachary, A. Chem. Mater. 2004, 16, 5336.
[30] Xu, Y. H.; Lu, J.; Loh, T. P. J. Am. Chem. Soc. 2009, 131, 1372.
[31] Shirai, M.; Mitsukura, K.; Okamura, H. Chem. Mater. 2008, 20, 1971.
/
| 〈 |
|
〉 |
