Citation: Wang Zichao, Xu Youjun, Shi Shiliang. Base-Promoted Rapid Hydrosilylation of Aldimine[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3463-3466. doi: 10.6023/cjoc202005085 shu

Base-Promoted Rapid Hydrosilylation of Aldimine

Wang Zichao ^a,b ,
Xu Youjun ^b,, ,
Shi Shiliang ^a,,

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

Corresponding author: Xu Youjun, xuyoujun@syphu.edu.cn Shi Shiliang, shiliangshi@sioc.ac.cn
Received Date: 29 May 2020
Revised Date: 3 July 2020
Available Online: 22 June 2020
Fund Project: the National Natural Science Foundation of China 21871288the National Natural Science Foundation of China 91856111the National Natural Science Foundation of China 21821002the Strategic Priority Research Program of the Chinese Academy of Sciences XDB20000000the National Natural Science Foundation of China 21690074Project 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)

Figures(2)

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.
- hydrosilylation,
- aldimine,
- rapid reaction,
- base catalysis
1. [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. [2]
  Nugent, T. C.; El-Shazly, M. Adv. Synth. Catal. 2010, 352, 753. doi: 10.1002/adsc.200900719
3. [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. [4]
5. [5]
  Zhu, C.; Saito, K.; Yamanaka, M.; Akiyama, T. Acc. Chem. Res. 2015, 48, 388. doi: 10.1021/ar500414x
6. [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. [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. [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. [9]
10. [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. [11]
  Revunova, K.; Nikonov, G. I. Chem.-Eur. J. 2014, 20, 839. doi: 10.1002/chem.201302728
12. [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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