SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 8: 2394 - 2401

DOI: https://doi.org/10.6023/cjoc202004019

研究论文

铑催化的丙酮肟醚导向的苯酚的邻位烯基化反应

  • 刘玲玲 ,
  • 杨闪 ,
  • 韩昳 ,
  • 戴晨阳 ,
  • 史达清 ,
  • 黄志斌 ,
  • 赵应声
展开
  • 苏州大学材料与化学化工学部 苏州 215123

收稿日期: 2020-04-13

  修回日期: 2020-05-22

  网络出版日期: 2020-06-01

基金资助

国家自然科学基金（Nos.21772139，21572149）、江苏省高等学校自然科学基金重大基础研究（Nos.15KJA150006，17KJA150006）、江苏省杰出青年自然科学基金（No.BK2018g0041）、苏州科技基础设施（No.SZS2018201708）和江苏高校优势学科建设工程资助项目.

收起

Rhodium-Catalyzed ortho-Alkenylation of Phenols Directed by Acetone Oxime Ether

  • Liu Lingling ,
  • Yang Shan ,
  • Han Yi ,
  • Dai Chenyang ,
  • Shi Daqing ,
  • Huang Zhibin ,
  • Zhao Yingsheng
Expand
  • College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received date: 2020-04-13

  Revised date: 2020-05-22

  Online published: 2020-06-01

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21772139, 21572149), the Major Basic Research Project of the Natural Science Foundation of Jiangsu Higher Education Institutions (Nos. 15KJA150006, 17KJA150006), the Jiangsu Province Natural Science Found for Distinguished Young Scholars (No. BK2018g0041), the Project of Scientific and Technologic Infrasracture of Suzhou (No. SZS2018201708) and the Priority Academic Program Development of Jiangsu Higher Education Institutions Project.

Fold

摘要

以弱配位中心丙酮肟醚为导向基团，Rh为催化剂，实现了一种高区域选择性的苯酚类化合物邻位烯基化反应.该策略具有反应条件温和、底物适应性广、区域选择性好等优点.为苯酚的选择性的邻位烯基化提供了一种新的有效方法.

关键词： 苯酚; 丙酮肟醚; 烯基化

本文引用格式

刘玲玲 , 杨闪 , 韩昳 , 戴晨阳 , 史达清 , 黄志斌 , 赵应声 . 铑催化的丙酮肟醚导向的苯酚的邻位烯基化反应[J]. 有机化学, 2020 , 40(8) : 2394 -2401 . DOI: 10.6023/cjoc202004019

Abstract

A practical rhodium-catalyzed highly regioselective ortho-alkenylation of phenolic compound under the assistance of weak coordination center acetoxime ether was developed. This strategy has advantages of simple and mild reaction conditions, wide scope of substrate and high regioselectivity. This protocol provids an efficient and new method for the regioselective ortho-alkenylation of phenols.

Key words： phenol; acetone oxime ether; alkenylation

参考文献

[1] (a) Zhou, P. P.; Guan, M. Y.; Zhang, J. Y.; Xu, F.; Zhao, Y. S. Chin. J. Org. Chem. 2017, 37, 2028(in Chinese). (周盼盼, 管明玉, 张静宇, 徐凡, 赵应声, 有机化学, 2017, 37, 2028.)
(b) Zheng, Y. X.; Han, J.; Huang, Z. B.; Shi, D. Q.; Zhao, Y. S. Chin. J. Org. Chem. 2017, 37, 2066(in Chinese). (郑永祥, 韩健, 黄志斌, 史达清, 赵应声, 有机化学, 2017, 37, 2066.)
(c) 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.)
(d) 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.)
[2] (a) Gou, Q.; Tan, X. P.; Zhang, M. Z.; Ran, M.; Yuan, T. R.; He, S. H.; Zhou, L. Z.; Cao, T. W.; Luo, F. H. Org. Lett. 2020, 22, 1966.
(b) Dai, J.-L.; Shao, N.-Q.; Zhang, J.; Jia, R.-P.; Wang, D.-H. J. Am. Chem. Soc. 2017, 139, 12393.
(c) Fabry, D. C.; Ronge, M. A.; Zoller, J.; Rueping, M. Angew. Chem., Int. Ed. 2015, 54, 2801.
(d) Zhang, L.; Zhu, L.; Zhang, Y.; Yang, Y.; Wu, Y.; Ma, W.; Lan, Y.; You, J. ACS Catal. 2018, 8. 8324.
(e) Khaefa, S.; Rostamic, A.; Khakyzadehd, V.; Zolfigolb, M. A.; Taherpoura, A. A.; Yarieb, M. Mol. Catal. 2020, 484, 110772.
[3] Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Veries J.-G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
[4] Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. J. Am. Chem. Soc. 2006, 128, 2528.
[5] Wu, J. L.; Cui, X. L.; Chen, L. M.; Jiang, G. J.; Wu, Y. G. J. Am. Chem. Soc. 2009, 131, 13888.
[6] Wang, D. H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315.
[7] Xu, W. T.; Wang, N.; Zhang, M. Y.; Shi, D. Q. Chin. J. Org. Chem. 2019, 39, 1735(in Chinese). (徐文韬, 王宁, 张梦烨, 史达清, 有机化学, 2019, 39, 1735.)
[8] Ackermann, L.; Pospech, J. Org. Lett. 2011, 13, 4153.
[9] Padala, K.; Jeganmohan, M. Org. Lett. 2011, 13, 6144.
[10] Hashimoto, Y.; Hirano, K.; Satoh, T.; Kakiuchi, F.; Miura, M. Org. Lett. 2012, 14, 2058.
[11] Manikandan, R.; Madasamy, P.; Jeganmohan, M. ACS Catal. 2016, 6, 230.
[12] Dana, S.; Mandal, A.; Sahoo, H.; Mallik, S.; Grandhi, G.-S.; Baidya, M. Org. Lett. 2018, 20, 716.
[13] Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9982.
[14] Yin, B.; Fu, M.-L.; Zhu, Q. Chin. J. Org. Chem. 2020, 40, 1461(in Chinese). (尹彪, 付曼琳, 朱勍, 有机化学, 2020, 40, 1461.)
[15] Wang, C. M.; Chen, H.; Wang, Z. F.; Chen, J. A.; Huang, Y. Angew. Chem., Int. Ed. 2012, 51, 7242.
[16] Kona, C. N.; Nishii, Y.; Miura, M. Org. Lett. 2018, 20, 4898.
[17] Gan, F. F.; Chua, Y. S.; Scarmagnani, S.; Palaniappan, P.; Franks, M.; Poobalasingam, T.; Bradshaw, T. D.; Westwell, A. D.; Hagen, T. Res. Commun. 2009, 387, 741.
[18] Tyman, J. H. P. Synthetic and Natural Phenols, Elsevier, New York, 1996.
[19] Finkelstein, B. L.; Benner, E. A.; Hendrixson, M. C.; Kranis, K. T.; Rauh, J. J.; Sethuraman, M. R.; McCann, S. F. Bioorg. Med. Chem. 2002, 10, 599.
[20] Martín Castro, A. M. Chem. Rev. 2004, 104, 2939.
[21] (a) Reddy, M. C.; Jeganmohan, M. Eur. J. Org. Chem. 2013, 1150.
(b) Li, B.; Ma, J.; Liang, Y.; Wang, N.; Xu, S.; Song, H.; Wang, B. Eur. J. Org. Chem. 2013, 1950.
(c) Dai, H.-X.; Li, G.; Zhang, X.-G.; Stepan, A. F.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 7567.
[22] Huang, C. H.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 12406.
[23] Gong, T.-J.; Xiao, B.; Liu, Z.-J.; Wan, J.; Xu, J.; Luo, D.-F.; Fu, Y.; Liu, L. Org. Lett. 2011, 13, 3235.
[24] Shen, Y. Y.; Liu, G. X.; Zhou, Z.; Lu, X. Y. Org. Lett. 2013, 15, 3366.
[25] Bolotin, D. S.; Bokach, N. A.; Demakova, M. Y.; Kukushkin, V. Y.; Chem. Rev. 2017, 117, 13039.
[26] Singh, N.; Karpichev, Y.; Tiwari, A. K.; Kuca, K.; Ghosh, K. K.; J. Mol. Liq. 2015, 208, 307.
[27] Worek, F.; Thiermann, H.; Wille, T. Chem.-Biol. Interact. 2016, 259, 93.
[28] Guo, K.; Chen, X. L.; Guan, M. Y.; Zhao, Y. S. Org. Lett. 2015, 17, 1802.
[29] Liu, L. L.; Wang, N.; Dai, C. Y.; Han, Y.; Yang, S.; Huang, Z. B.; Zhao, Y. S. Eur. J. Org. Chem. 2019, 7857.
[30] Wang, N.; Liu, L. L.; Xu, W. T.; Zhang, M. Y.; Huang, Z. B.; Shi, D. Q.; Zhao, Y. S. Org. Lett. 2019, 21, 365.
[31] Zhou, B.; Chen, Z. Q.; Yang, Y. X.; Ai, W.; Tang, H. Y.; Wu, Y. X.; Zhu, W. L.; Li, Y. C. Angew. Chem., Int. Ed. 2015, 54, 12121.
[32] Xie, F.; Qi, Z. S.; Yu, S. J.; Li, X. W. J. Am. Chem. Soc. 2014, 136, 4780.
[33] Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433.
[34] Hyster, T. K.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 10565.
[35] Liu, B.; Fan, Y.; Gao, Y.; Sun, C.; Xu, C.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 468.
[36] Xu, L.; Zhu, Q.; Huang, G.; Cheng, B.; Xia, Y. J. Org. Chem. 2012, 77, 3017.
[37] Takeda, N.; Miyata, O.; Naito, T. Eur. J. Org. Chem. 2007, 1491.
[38] Rao, M. L. N.; Ramakrishna, B. S. J. Org. Chem. 2019, 84, 5677.
[39] Liu, B.; Jiang, H. Z.; Shi, B. F. J. Org. Chem. 2014, 79, 1521.
[40] Chen, J. M.; Liu, W.; Zhou, L. D.; Zhao, Y. L. Tetrahedron Lett. 2018, 59, 2526.
[41] Ribeiro Laia, F. M.; Pinho e Melo, T. M. V. D. Synthesis 2015, 47, 2781.
[42] Jiang, Q.; Xu, B.; Jia, J.; Zhao, A.; Zhao, Y. R.; Li, Y. Y.; He, N. N.; Guo, C. C. J. Org. Chem. 2014, 79, 7372.
Options
文章导航

/

〈 〉