草酰胺导向下钯催化的C(sp2)—H和C(sp3)—H键的直接酰氧基化反应
收稿日期: 2017-01-16
修回日期: 2017-03-22
网络出版日期: 2017-04-13
基金资助
国家自然科学基金(Nos.21403148,21572149)和江苏省高校自然科学重大研究(No.15KJA150006)资助项目.
Palladium-Catalyzed Direct Acyloxylation of C (sp2)—H and C (sp3)—H Bonds under the Assistance of Oxalyl Amide
Received date: 2017-01-16
Revised date: 2017-03-22
Online published: 2017-04-13
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21403148, 21572149) and the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 15KJA150006).
郑永祥 , 韩健 , 黄志斌 , 史达清 , 赵应声 . 草酰胺导向下钯催化的C(sp2)—H和C(sp3)—H键的直接酰氧基化反应[J]. 有机化学, 2017 , 37(8) : 2066 -2072 . DOI: 10.6023/cjoc201701032
A practical palladium-catalyzed direct acyloxylation of C(sp2)—H and C(sp3)—H bonds under the assistance of oxalyl amide with TBPB as oxidant was developed. Selective acyloxylation of C(sp2)—H bond for oxalyl amide protected benzyl amine using TBPB or carboxylic acids as acyloxylating reagent was achieved. For oxalyl amide protected 2-alkylanilines, the selective acyloxylation of benzylic C(sp3)—H bond was also achieved. This protocol provided an efficient and practical method for the synthesis of aryl esters.
Key words: acyloxylation; C(sp2)—H bond; C(sp3)—H bond
[1] Engle, K. M.; Mei, T. S.; Wasa, M.; Yu, J. Q. Acc. Chem. Res. 2011, 45, 788.
[2] Bariwal, J.; Van der Eycken, E. Chem. Soc. Rev. 2013, 42, 9283.
[3] Louillat, M. L.; Patureau, F. W. Chem. Soc. Rev. 2014, 43, 901.
[4] Shang, X. J.; Liu, Z. Q. Chin. J. Org. Chem. 2015, 35, 522(in Chinese). (尚筱洁, 柳忠全, 有机化学, 2015, 35, 522.)
[5] Shang, X. J.; Liu, Z. Q. Chem. Soc. Rev. 2013, 42, 3253.
[6] Luo, F. H.; Long, Y.; Li, Z. K.; Zhou, X. G. Acta Chim. Sinica 2016, 74, 805(in Chinese). (罗飞华, 龙洋, 李正凯, 周向葛, 化学学报, 2016, 74, 805.)
[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] Xu, J. B.; Chen, P. H.; Ye, J. X.; Liu, G. S. Acta Chim. Sinica 2015, 73, 1294(in Chinese). (徐佳斌, 陈品红, 叶金星, 刘国生, 化学学报, 2015, 73, 1294.)
[9] Li, T. T.; Yu, P.; Lin, J. S.; Zhi, Y. G.; Liu, X. Y. Chin. J. Chem. 2016, 34, 490.
[10] Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
[11] Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J. Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
[12] 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.)
[13] He, J. Q.; Lou, S. J.; Xu, D. Q. Chin. J. Org. Chem. 2016, 36, 1218(in Chinese). (何将旗, 娄绍杰, 许丹倩, 有机化学, 2016, 36, 1218.)
[14] 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.)
[15] Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
[16] Kalyani, D.; Sanford, M. S. Org. Lett. 2005, 7, 4149.
[17] Chen, X.; Hao, X. S.; Goodhue, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 6790.
[18] Wang, W. H.; Luo, F.; Zhang, S. H.; Cheng, J. J. Org. Chem. 2010, 75, 2415.
[19] Roane, J.; Daugulis, O. Org. Lett. 2013, 15, 5842.
[20] Wang, Z.; Kuninobu, Y.; Kanai, M. Org. Lett. 2014, 16, 4790.
[21] Wu, X. S.; Zhao, Y.; Ge, H. B. Chem. Asian J. 2014, 9, 2736.
[22] Zhao, S.; Chen, F. J.; Liu, B.; Shi, B. F. Sci. China Chem. 2015, 58, 1302.
[23] Wang, C.; Chen, C. P.; Zhang, J. Y.; Han, J.; Wang, Q.; Guo, K.; Liu, P.; Guan, M. Y.; Yao, Y. M.; Zhao, Y. S. Angew. Chem., Int. Ed. 2014, 53, 9884.
[24] Wang, Q.; Han, J.; Wang, C.; Zhang, J. Y.; Huang, Z. B.; Shi, D. Q.; Zhao, Y. S. Chem. Sci. 2014, 5, 4962.
[25] Han, J.; Liu, P.; Wang, C.; Wang, Q.; Zhang, J. Y.; Zhao, Y. W.; Shi, D. Q.; Huang, Z. B.; Zhao, Y. S. Org. Lett. 2014, 16, 5682.
[26] Chen, C. P.; Wang, C.; Zhang, J. Y.; Zhao, Y. S. J. Org. Chem. 2015, 80, 942.
[27] Liu, P.; Han, J.; Chen, C. P.; Shi, D. Q.; Zhao, Y. S. RSC Adv. 2015, 5, 28430.
[28] Hu, J. D.; Li, G. B.; Yuan, C. C.; Huang, Z. B.; Shi, D. Q.; Zhao, Y. S. J. Org. Chem. 2016, 18, 5998.
/
〈 |
|
〉 |