Base-Promoted Rapid Hydrosilylation of Aldimine

doi:10.6023/cjoc202005085

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3463-3466.DOI: 10.6023/cjoc202005085 Previous Articles Next Articles

Special Issue: 有机硅化学虚拟合辑；黄乃正院士七十华诞专辑

碱促进醛亚胺的快速氢硅化反应

王子超^a,b, 许佑君^b, 施世良^a

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 发布日期:2020-07-23
通讯作者: 许佑君, 施世良 E-mail:shiliangshi@sioc.ac.cn;xuyoujun@syphu.edu.cn
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.

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

Received:2020-05-29 Revised:2020-07-03 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).

1. 203463S.pdf(1293KB)

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

Cite this article

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

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.

[1]	Zijie Song, Jun Liu, Ying Bai, Jiayun Li, Jiajian Peng. Progress in Catalysis Transformation of Carbon Dioxide through Hydrosilylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2068-2080.
[2]	Xiangqing Feng, Haifeng Du. B(C₆F₅)₃-Catalyzed Silylation of Unsaturated Hydrocarbons [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3544-3557.
[3]	Jiajie Zhu, Yi Wan, Qiyang Yuan, Jinlian Wei, Yongqiang Zhang. Research of Visible Light/Lewis Base Dual Catalytic Defluorinative Silylation of Trifluoromethyl-Substituted Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3623-3634.
[4]	Jun Liu, Jiajian Peng, Ying Bai, Jiayun Li, Zijie Song, Peng Liu, Ting Ouyang, Huilin Lan. Progress in Photocatalytic Hydrosilylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3558-3568.
[5]	Peifeng Su, Jinyu Ni, Zhuofeng Ke. Recent Advances in Homogeneous Catalytic Systems for CO₂Hydrosilylation and Related Transformations [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3526-3543.
[6]	Fengjuan Chen, Luo Liu, Zilu Zhang, Wei Zeng. Recent Progress in Synthesis of Organosilanes Driven by Visible-Light [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3454-3469.
[7]	Wei Sun, Shoufei Zhu. Hydrosilylation Reactions of Alkene with Tertiary Silanes Catalyzed by Iron-Series Metals [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3339-3351.
[8]	JIan Xiao, Zhiying Wu, Ziyi Chen, Pengfei Zhao. Tetraethylenepentamine Functionalized Phenolic Resin as Highly Active Acid-Base Bifunctional Catalyst for Knoevenagel Condensation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1179-1187.
[9]	Xin Li, Qiuling Song. Chiral Borane-Catalyzed Enantioselective Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3143-3151.
[10]	Ziyan Shao, Qingli Zhou, Jiancheng Wang, Rui Tang, Yuehai Shen. Sodium Iodide-Triphenylphosphine-Mediated Photoredox Alkylation of Aldimines [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2676-2683.
[11]	Shurui Zhou, Kaige Wen, Xingping Zeng. Recent Progress in Catalytic Asymmetric Alkynylation of Imines [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 471-489.
[12]	Dai Zinan, Yu Zehao, Bai Ying, Li Jiayun, Peng Jiajian. Progress in Catalysis of Hydrosilylation by Cobalt Complexes [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1177-1187.
[13]	Wang Qiaotian, Han Caifang, Feng Xiangqing, Du Haifeng. Chiral Spiro Dienes Derived Boranes for Asymmetric Hydrosilylation of Ketones [J]. Chin. J. Org. Chem., 2019, 39(8): 2257-2263.
[14]	Luan Huaxin, Sun Hongjian, Xue Benjing, Li Xiaoyan. Synthesis and Properties of a Se-Coordinated Hydrido Cobalt(III) Complex Supported by Trimethylphosphine [J]. Chin. J. Org. Chem., 2017, 37(6): 1392-1397.
[15]	Zhang Feng, Liu Xianghua, Liu Wei, Deng Guojun. Application of Pd-Monodentate Phosphorus Catalysts in the Asymmetric Hydrosilylation Reactions of Alkenes [J]. Chin. J. Org. Chem., 2017, 37(10): 2555-2568.

碱促进醛亚胺的快速氢硅化反应

Base-Promoted Rapid Hydrosilylation of Aldimine

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments