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2020 , Vol. 40 >Issue 10: 3463 - 3466

DOI: https://doi.org/10.6023/cjoc202005085

研究简报

碱促进醛亚胺的快速氢硅化反应

  • 王子超 ,
  • 许佑君 ,
  • 施世良
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  • a 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032;
    b 沈阳药科大学 基于靶点的药物设计与研究教育部重点实验室 沈阳 110016

收稿日期: 2020-05-29

  修回日期: 2020-07-03

  网络出版日期: 2020-07-23

基金资助

中国科学院战略性先导科技专项（No.XDB20000000）和国家自然科学基金（Nos.21690074，21871288，91856111，21821002）资助项目.

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Base-Promoted Rapid Hydrosilylation of Aldimine

  • Wang Zichao ,
  • Xu Youjun ,
  • Shi Shiliang
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  • a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032;
    b Key Laboratory of Structure-Based Drug Design & Discovery, Shenyang Pharmaceutical University, Shenyang 110016

Received date: 2020-05-29

  Revised date: 2020-07-03

  Online published: 2020-07-23

Supported by

Project supported by the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000) and the National Natural Science Foundation of China (Nos. 21690074, 21871288, 91856111, 21821002).

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摘要

胺类化合物是一类重要的合成中间体，亚胺的氢硅化反应为胺类化合物的合成提供了一种便利的方法.过渡金属及主族元素催化剂在亚胺氢硅化反应中得到了广泛应用，然而，采用更加简单的反应条件实现这类反应更加具有实用价值.利用廉价易得的叔丁醇钾作为促进剂，实现了醛亚胺的快速还原反应，以良好的收率高效合成了一系列胺类化合物.该反应体系具有反应迅速，条件简单，实用高效的优点.

关键词： 氢硅化反应; 醛亚胺; 快速反应; 碱催化

本文引用格式

王子超 , 许佑君 , 施世良 . 碱促进醛亚胺的快速氢硅化反应[J]. 有机化学, 2020 , 40(10) : 3463 -3466 . DOI: 10.6023/cjoc202005085

Abstract

Amines are important intermediates in organic synthesis. The hydrosilylation of imines provides a convenient method for the synthesis of amines. Transition metal and main group catalysts have been widely applied in the hydrosilylation of imines. However, it would be more practical to use simpler reaction conditions to realize such reactions. In this paper, a fast hydrosilylation of aldimine was realized by using cheap t-BuOK as the promoter, providing an efficient method for the synthesis of amines in high yield. This reaction features rapid reaction, facile conditions, and robust practicability.

Key words： hydrosilylation; aldimine; rapid reaction; base catalysis

参考文献

[1] (a) Lawrence, S. A. Amines:Synthesis, Properties and Applications, Cambridge University, Press, Cambridge, 2004.
(b) Ricci, A. Amino Group Chemistry:Synthesis to the Life Sciences, Wiley-VCH, Weinheim, 2008.
[2] Nugent, T. C.; El-Shazly, M. Adv. Synth. Catal. 2010, 352, 753.
[3] (a) Das, S.; Wendt, B.; Möller, K.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2012, 51, 1662.
(b) Das, S.; Li, Y.; Bornschein, C.; Pisiewicz, S.; Kiersch, K.; Michalik, D.; Gallou, F.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2015, 54, 12389.
[4] (a) Spindler, F. Handbook of Homogeneous Hydrogention, Wiley-VCH, Weinheim, 2007.
(b) Hu, X.; Hu, F.; Zhang, M.; Liao, Y.; Xu, X.; Yuan, W.; Zhang, X. Chin. J. Org. Chem. 2016, 36, 1895(in Chinese). (扈晓艳, 胡方芝, 张敏敏, 廖益均, 徐小英, 袁伟成, 张晓梅, 有机化学, 2016, 36, 1895.)
(c) Wang, D.; Hou, C.; Chen, L.; Liu, X.; An, Q.; Hu, X. Chin. J. Org. Chem. 2013, 33, 1355(in Chinese). (王东, 侯传金, 陈丽凤, 刘小宁, 安庆大, 胡向平, 有机化学, 2013, 33, 1355.)
[5] Zhu, C.; Saito, K.; Yamanaka, M.; Akiyama, T. Acc. Chem. Res. 2015, 48, 388.
[6] (a) Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics 1998, 17, 3420.
(b) Takei, I.; Nishibayashi, Y.; Arikawa, Y.; Uemura, S.; Hidai, M. Organometallics 1999, 18, 2271.
[7] (a) Saini, A.; Smith, C. R.; Wekesa, F. S.; Helm, A. K.; Findlater, M. Org. Biomol. Chem., 2018, 16, 9368.
(b) Lipshutz, B. H.; Shimizu, H. Angew. Chem. Int. Ed. 2004, 43, 2228.
(c) Hansen, M. C.; Buchwald, S. L. Org. Lett., 2000, 2, 713.
[8] (a) Koller, J.; Bergman, R. G. Organometallics 2012, 31, 2530.
(b) Bezada, A.; Szewczyk, M.; Mlynarski, J. J. Org. Chem. 2016, 81, 336.
[9] (a) Chardon, A.; Rouden, J.; Blanchet, J. Eur. J. Org. Chem. 2019, 995.
(b) Prez, M.; Qu, Z.-W.; Caputo, C. B.; Podgorny, V.; Hounjet, L. J.; Hansen, A.; Dobrovetsky, R.; Grimme, S.; Stephan, D. W. Chem.-Eur. J. 2015, 21, 1.
(c) Müther, K.; Mohr, J.; Oestreich, M. Organometallics 2013, 32, 6643.
(d) Ge, X.; Chen, X.; Qian, C. Chin. J. Org. Chem. 2016, 36, 1208(in Chinese). (葛新, 陈新志, 钱超, 有机化学, 2016, 36, 1208.)
[10] (a) Wang, Z.-C.; Shen, D.; Gao, J. Jia, X.; Xu, Y.; Shi, S.-L. Chem. Commun. 2019, 55, 8848.
(b) Wang, Z.-C.; Wang, M.; Gao, J.; Shi, S.-L.; Xu Y. Org. Chem. Front. 2019, 6, 2949.
[11] Revunova, K.; Nikonov, G. I. Chem.-Eur. J. 2014, 20, 839.
[12] (a) Bagal, D. B; Watile, R. A; Khedkar, M. V.; Dhake, K. P.; Bhanage, B. M. Catal. Sci. Technol. 2012, 2, 354.
(b) Lee, C. C.; Liu, S. T. Chem. Commun. 2011, 47, 6981.
(c) Ohta, H.; Yuyama, Y.; Uozumi, Y.; Yamada, Y. M. A. Org. Lett. 2011, 13, 3892.
(d) Zhan, M.; Yang, H.; Zhang, Y.; Zhu, C.; Li, W.; Cheng, Y.; Hua, H. Chem. Commun. 2011, 47, 6605.
(e) Sousa, S. C. A.; Fernandes, A. C. Adv. Synth. Catal. 2010, 352, 2218.
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