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

doi:10.6023/cjoc201701032

有机化学 ›› 2017, Vol. 37 ›› Issue (8): 2066-2072.DOI: 10.6023/cjoc201701032 上一篇下一篇

研究论文

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

郑永祥, 韩健, 黄志斌, 史达清, 赵应声

苏州大学材料与化学化工学部苏州 215123

收稿日期:2017-01-16 修回日期:2017-03-22 发布日期:2017-04-13
通讯作者: 史达清, 赵应声 E-mail:dqshi@suda.edu.cn;yszhao@suda.edu.cn
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

Zheng Yongxiang, Han Jian, Huang Zhibin, Shi Daqing, Zhao Yingsheng

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received:2017-01-16 Revised:2017-03-22 Published:2017-04-13
Contact: 10.6023/cjoc201701032 E-mail:dqshi@suda.edu.cn;yszhao@suda.edu.cn
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).

文章分享

1. 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.PDF(1537KB)

摘要/Abstract

成功地发展了一种草酰胺导向的钯催化的过氧化苯甲酸叔丁酯为氧化剂的C（sp²）—H和C（sp³）—H键的酰氧基化反应.草酰胺基保护的苄胺用过氧化苯甲酸叔丁酯或羧酸为酰氧基化剂可以选择性地进行C（sp²）—H键的酰氧基化，而草酰氨基保护的2-烷基苯胺则可以进行苄基位C（sp³）—H键的酰氧基化反应.该方法为芳香酸酯类化合物的合成提供了一种方便、有效的方法.

关键词: 酰氧基化反应, C(sp³)—H键, C(sp²)—H键

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

引用此文

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.

Zheng Yongxiang, Han Jian, Huang Zhibin, Shi Daqing, Zhao Yingsheng. Palladium-Catalyzed Direct Acyloxylation of C (sp²)—H and C (sp³)—H Bonds under the Assistance of Oxalyl Amide[J]. Chin. J. Org. Chem., 2017, 37(8): 2066-2072.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[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.

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

Palladium-Catalyzed Direct Acyloxylation of C (sp²)—H and C (sp³)—H Bonds under the Assistance of Oxalyl Amide

PDF

补充材料

可视化

被引次数

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 3

编辑推荐

相关统计

本文评价

[1]	任林静, 冉茂刚, 方学红, 赵玲, 姚秋丽. 通过C(sp³)—H键直接官能团化高效合成1-芳基烯基膦酸酯[J]. 有机化学, 2018, 38(10): 2791-2797.
[2]	陈翠, 邱会华. 芳酮类化合物羰基邻位sp³-C-H键的乙酰氧基化反应研究[J]. 有机化学, 2016, 36(4): 826-829.
[3]	谭明雄, 顾运琼, 罗旭健, 张培. 导向的过渡金属催化不活泼C(sp³)—H键氧化反应研究进展[J]. 有机化学, 2015, 35(4): 781-788.