Synthesis and Catalytic Property of New Aminophosphino Ruthenium Carbonyl Complexes

doi:10.6023/cjoc201906022

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (1): 226-231.DOI: 10.6023/cjoc201906022 Previous Articles Next Articles

新型膦胺配体羰基钌化合物的合成及其催化性能研究

方霄龙^a,b, 章敏^a, 段宁^a, 汪新^a, 朱红平^b

a 池州学院化学与材料工程学院微纳粉体与先进能源材料安徽普通高校重点实验室安徽池州 247000;
b 厦门大学化学化工学院固体表面物理化学国家重点实验室醇醚酯清洁生产国家工程实验室福建厦门 361005

收稿日期:2019-06-18 修回日期:2019-08-22 发布日期:2019-09-12
通讯作者: 汪新, 朱红平 E-mail:wangxin164@sina.com;hpzhu@xmu.edu.cn
基金资助:
国家自然科学基金（Nos.21802010，21673191）、安徽省自然科学基金（No.1808085QB48）及池州学院青年教师科研启动基金（No.2018YJRC001）资助项目.

Synthesis and Catalytic Property of New Aminophosphino Ruthenium Carbonyl Complexes

Fang Xiaolong^a,b, Zhang Min^a, Duan Ning^a, Wang Xin^a, Zhu Hongping^b

a Key Laboratory of Micro-nano Powder and Advanced Energy Materials of Anhui Higher Education Institutes, College of Chemistry and Materials Engineering, Chizhou University, Chizhou, Anhui 247000;
b State Key Laboratory of Physical Chemistry of Solid Surfaces, National Engineering Laboratory for Green Chemical Productions of Alcohols-Ethers-Esters, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005

Received:2019-06-18 Revised:2019-08-22 Published:2019-09-12
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21802010, 21673191), the Natural Science Foundation of Anhui Province (No. 1808085QB48) and the Starting Grants for Young Teachers of Chizhou University (No. 2018YJRC001).

1. 200226S.pdf.pdf(580KB)

Abstract

New carbonyl ruthenium complexes (μ-o-PPh₂C₆H₄NH)Ru₃(μ-H)(CO)₉ (2), (o-PPh₂C₆H₄NH)₂Ru(CO)₂ (3) and (μ-o-PPh₂C₆H₄NMe₂)₂Ru(CO)₃ (4) have been successfully synthesized by using ruthenium carbonyl and o-PPh₂C₆H₄NR₂ (R=H, Me) ligand. The three complexes have all been characterized by NMR and IR spectroscopies, elemental analysis and X-ray crystallography. Complexes 2 and 4 could catalyze the hydrogenation of benzaldehyde into benzyl alcohol. However, complex 3 showed no activity. This study reveals a correlation between structure and catalytic property, where the possible deactivation mode for the hydrogenation reaction using the aminophosphino ruthenium catalyst is discussed in view of the experimental work.

Key words: aminophosphino ruthenium carbonyl, synthesis and characterization, catalytic hydrogenation, structure and property, deactivation

Cite this article

Fang Xiaolong, Zhang Min, Duan Ning, Wang Xin, Zhu Hongping. Synthesis and Catalytic Property of New Aminophosphino Ruthenium Carbonyl Complexes[J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 226-231.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Dub, P. A.; Ikariya, T. ACS Catal. 2012, 2, 1718.
(b) Werkmeister, S.; Junge, K.; Beller, M. Org. Process Res. Dev. 2014, 18, 289.
(c) Pritchard, J.; Filonenko, G. A.; van Putten, R.; Hensen, E. J. M.; Pidko, E. A. Chem. Soc. Rev. 2015, 44, 3808.
(d) Zhang, Y. W.; Chen, Y. L.; Fang, X. L.; Yuan, Y. Z.; Zhu, H. P. Chin. J. Org. Chem. 2017, 37, 2275(in Chinese). (张亦伟, 陈艺林, 方霄龙, 袁友珠, 朱红平, 有机化学, 2017, 37, 2275.)
[2] (a) Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490.
(b) Saudan, L. A.; Saudan, C. M.; Debieux, C.; Wyss, P. Angew. Chem., Int. Ed. 2007, 46, 7473.
(c) Han, Z.; Rong, L.; Wu, J.; Zhang, L.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2012, 51, 13041.
(d) Zhao, B.; Han. Z.; Ding. K. Angew. Chem., Int. Ed. 2013, 52, 4744.
(e) Tan, X.; Wang, Y.; Liu, Y.; Wang, F.; Shi, L.; Lee, K. H.; Lin, Z.; Lv, H.; Zhang, X. Org. Lett. 2015, 17, 454.
[3] (a) Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2006, 45, 1113.
(b) Balaraman, E.; Gunanathan, C.; Zhang, J.; Shimon, L. J. W.; Milstein, D. Nat. Chem. 2011, 3, 609.
(c) Gunanathan, C.; Milstein, D. Acc. Chem. Res. 2011, 44, 588.
(d) Li, W.; Xie, J. H.; Yuan, M. L.; Zhou, Q. L. Green Chem. 2014, 16, 4081.
[4] (a) Hanton, M. J.; Tin, S.; Boardman, B. J.; Miller, P. J. Mol. Catal. A:Chem. 2011, 346, 70.
(b) vom Stein, T.; Meuresch, M.; Limper, D.; Schmitz, M.; Hölscher, M.; Coetzee, J.; Cole-Hamilton, D. J.; Klankermayer, J.; Leitner, W. J. Am. Chem. Soc. 2014, 136, 13217.
[5] (a) Fang, X.; Zhang, C.; Chen, J.; Zhu, H.; Yuan, Y. RSC Adv. 2016, 6, 45512.
(b) Fang, X.; Sun, M.; Zheng, J.; Li, B.; Ye, L.; Wang, X.; Cao, Z.; Zhu, H.; Yuan, Y. Sci. Rep. 2017, 7, 3961.
(c) Fang, X.; Li, B.; Zheng, J.; Wang, X.; Zhu, H.; Yuan, Y. Dalton Trans. 2019, 48, 2290.
[6] Fang, X.; Duan, N.; Zhang, M.; Zhang, C.; Liu, R.; Zhu, H. P. Chin. J. Org. Chem. 2019, 39, 1450(in Chinese). (方霄龙, 段宁, 章敏, 张春燕, 刘睿, 朱红平, 有机化学, 2019, 39, 1450.)
[7] Mason, R.; Rae, A. I. M. J. Chem. Soc. A 1968, 778.
[8] (a) Deeming, A. J.; Martin, C. M. Angew. Chem., Int. Ed. 1998, 37, 1691.
(b) Hanif, K. M.; Hursthouse, M. B.; Kabir, S. E.; Malik, K. M. A.; Rosenberg, E. J. Organomet. Chem. 1999, 580, 60.
(c) Tan, X.; Li, B.; Xu, S.; Song, H.; Wang, B. Organometallics 2011, 30, 2308.
[9] Gong, P.; Wu, B.; Liu, S.; Wang, D. Chin. J. Inorg. Chem. 2004, 20, 37(in Chinese). (宫培军, 吴秉芳, 刘树堂, 王丁泽, 无机化学学报, 2004, 20, 37.)
[10] Teunissen, H. T.; Elsevier, C. J. Chem. Commun. 1997, 667.
[11] (a) El-Amouri, H.; Bahsoun, A. A.; Fischer, J.; Osborn, J. A. Angew. Chem., Int. Ed. 1987, 26, 1169.
(b) Holland, G. F.; Ellis, D. E.; Tyler, D. R.; Gray, H. B.; Trogler, W. C. J. Am. Chem. Soc. 1987, 109, 4276.
[12] (a) Van der Sluys, L. S.; Kubas, G. J.; Caulton, K. G. Organometallics 1991, 10, 1033.
(b) Chen, Y. Z.; Chan, W. C.; Lau, C. P.; Chu, H. S.; Lee, H. L.; Jia, G. Organometallics 1997, 16, 1241.
[13] (a) Herd, O.; Heßler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69.
(b) Richard, V.; Ipouck, M.; Mérel, D. S.; Gaillard, S.; Whitby, R. J.; Witulski, B.; Renaud, J. L. Chem. Commun. 2014, 50, 593.

[1]	Chen Zhikang, Mao Yuanhong, Cao Yucai, Liang Shengbiao, Song Sha, Ni Chen, Liu Zhenyu, Ye Xiaofeng, Shen An, Zhu Hongping. Metallocene Catalyst Systems and Control over the Propylene Polymerization [J]. Chin. J. Org. Chem., 2018, 38(11): 2937-2992.
[2]	Li Yong, Wang Zheng, Liu Qingbin. Progress in Homogeneous Catalytic Hydrogenation of CO₂ [J]. Chin. J. Org. Chem., 2017, 37(8): 1978-1990.
[3]	Wang Hui, Zheng Yi, Pan Zhentao, Fu Hongliang, Ling Fei, Zhong Weihui. Progress of Frustrated Lewis Pairs in Catalytic Hydrogenation [J]. Chin. J. Org. Chem., 2017, 37(2): 301-313.
[4]	Wang Qinting, Zhao Shuai, Jin Lei, Chen Xin. Synthesis of Fmoc-protected (S)-3,5-Dibromophenylalanine in the Presence of a Phase Transfer Catalyst or a Chiral Catalyst [J]. Chin. J. Org. Chem., 2016, 36(9): 2242-2246.
[5]	Cheng Yinan, Xie Guiying, Sun Shujun, You Xiufeng. A Practical Synthesis of 3-{[4-(2,6-Dichlorophenyl)piperidin-1-yl]- methyl}-2-(thiophen-2-yl)-1H-indole as a New Ligand for Opioid Receptor Like 1 Receptor [J]. Chin. J. Org. Chem., 2013, 33(03): 630-633.
[6]	Ma Kaiqing, Zhang Chunbo, Liu Mingming, Chu Yong, Hu Changqi, Ye Deyong. Asymmetric Total Synthesis of 4(15)-Eudesmene-1β,7α-diol [J]. Chin. J. Org. Chem., 2012, 32(04): 781-785.
[7]	WANG Ping-An, SUN Xiao-Li, GAO Peng. Frustrated Lewis Pairs: A New Strategy for Metal-Free Catalytic Hy-drogenation [J]. Chin. J. Org. Chem., 2011, 31(9): 1369-1376.
[8]	ZHANG Fan, LI Yun-Qing, WANG Jia-Xi. PMHS/RuCl₃ as an Efficient System for Reduction of Amide to Amine [J]. Chin. J. Org. Chem., 2010, 30(12): 1921-1924.
[9]	MA Run-Zhi, LI Yun-Qiang, ZHOU Hong-Yong, WANG Jia-Chi. Preparation of N,N-Dibutylformylamide—Hydrogenation of Carbon Dioxide in Presence of Dibutylamine [J]. Chin. J. Org. Chem., 2009, 29(11): 1843-1848.
[10]	GONG Da-Chun*^,a,b,ZHOU Hua^b,WEI Ping^b, WANG Tai-Shan^c,OUYANG Ping-Kai^b. Synthesis of Aminophosphine Phosphinite Ligand Bis(oxaza-phospholano)-ethane with C₂-Symmetric Axis and Its Application in Asymmetric Hydrogenation [J]. Chin. J. Org. Chem., 2008, 28(04): 638-643.
[11]	LIU Peng, JIANG Huan-Feng. Progress in Asymmetric Hydrogenation of Prochiral Schiff Base [J]. Chinese Journal of Organic Chemistry, 2004, 24(10): 1317-1322.
[12]	Chen Xiangqun;Huang Yudong;Li Dawei. Synthesis and Purification of 2,6-Bis(p-aminophenyl)-benzo[1,2-d;5, 4-d']bisoxazole [J]. Chin. J. Org. Chem., 2003, 23(11): 1306-1308.
[13]	Wang Keqiang;Sun Xianzhong. Calculating the refractive index of alkane and cycloalkane using the group bond contribution method [J]. Chin. J. Org. Chem., 2001, 21(2): 144-149.
[14]	Qin Jingui. Molecular design, synthesis an dproperties of some new organic and organometallic electro-active materials [J]. Chin. J. Org. Chem., 2001, 21(11): 1081-1089.
[15]	Wang Keqiang;Wang Jie. A new group contribution method for calculating the boiling point of alkane [J]. Chin. J. Org. Chem., 2001, 21(10): 751-754.

新型膦胺配体羰基钌化合物的合成及其催化性能研究

Synthesis and Catalytic Property of New Aminophosphino Ruthenium Carbonyl Complexes

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments