聚乙二醇-水介质中水溶性膦稳定的钌催化芳香酮的不对称加氢反应

doi:10.3724/SP.J.1088.2011.10434

催化学报 ›› 2011, Vol. 32 ›› Issue (9): 1490-1495.DOI: 10.3724/SP.J.1088.2011.10434

聚乙二醇-水介质中水溶性膦稳定的钌催化芳香酮的不对称加氢反应

秦瑞香 1, 王金波 1,2,a, 熊伟 1, 刘德蓉 1, 冯建 1, 陈华 2,b

1重庆科技学院化学化工学院, 重庆 401331; 2四川大学化学学院, 绿色化学及技术教育部重点实验室, 四川成都 610064

收稿日期:2011-04-21 修回日期:2011-05-18 出版日期:2011-09-09 发布日期:2015-01-24

Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Achiral Monophosphine TPPTS-Stabilized Ru in PEG-Water

QIN Ruixiang1, WANG Jinbo1,2,a, XIONG Wei1, LIU Derong1, FENG Jian1, CHEN Hua2,b

1College of Chemistry and Chemical Engineering, Chongqing University of Science and Technology, Chongqing 401331, China; 2Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, Sichuan, China

Received:2011-04-21 Revised:2011-05-18 Online:2011-09-09 Published:2015-01-24

摘要/Abstract

摘要： 在聚乙二醇-400-水介质中, 以 (1S,2S)-1,2-二苯基乙二胺的磺酸钠盐为手性修饰剂, 考察了水溶性三 (间-磺酸钠苯基) 膦稳定的 Ru 催化苯乙酮及其衍生物的不对称加氢反应. 结果表明, 该催化剂体系具有良好的催化活性和对映选择性. 在优化反应条件下, 苯乙酮转化率和对映选择性分别为 100% 和 84.9%. 经正己烷萃取后, 催化剂即可从产物中分离出来, 并可重复使用多次.

关键词: 水溶性膦稳定的钌, 芳香酮, 不对称加氢, 芳香仲醇, 聚乙二醇-水

Abstract: PEG-400 was found to be a green and recyclable reaction medium for asymmetric hydrogenation of aromatic ketones catalyzed by achiral monophosphine TPPTS (P(m-C₆H₄SO₃Na)₃), stabilized ruthenium modified by (1S,2S)-DPENDS (DPENDS: disodium salt of sulfonated (1S,2S)-1,2-diphenyl-1,2-ethylene-diamine). A 84.9% ee was obtained for acetophenone under the optimized conditions. The resulting products can be easily separated from the catalyst by extraction with n-hexane. The catalyst immobilized on PEG-400 not only exhibits excellent activity and enantioselectivity but also can be recycled and reused several times without loss of activity and enantioselectivity.

Key words: TPPTS-stabilized ruthenium, aromatic ketone, asymmetric hydrogenation, aromatic sec-alcohol, polyethylene glycol-400-water

秦瑞香, 王金波, 熊伟, 刘德蓉, 冯建, 陈华. 聚乙二醇-水介质中水溶性膦稳定的钌催化芳香酮的不对称加氢反应[J]. 催化学报, 2011, 32(9): 1490-1495.

QIN Rui-Xiang, WANG Jin-Bo, XIONG Wei, LIU De-Rong, FENG Jian, CHEN Hua. Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Achiral Monophosphine TPPTS-Stabilized Ru in PEG-Water[J]. Chinese Journal of Catalysis, 2011, 32(9): 1490-1495.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.3724/SP.J.1088.2011.10434

https://www.cjcatal.com/CN/Y2011/V32/I9/1490

参考文献

1Ohkuma T, Koizumi M, Doucet H, Pham T, Kozawa M, Murata K, Katayama E, Yokozawa T, Ikariya T, Noyori R. J Am Chem Soc, 1998, 120: 13529
2Ohkuma T, Ishii D, Takeno H, Noyori R. J Am Chem Soc, 2000, 122: 6510
3Ohkuma T, Koizumi M, Muniz K, Hilt G, Kabuto C, Noyori R. J Am Chem Soc, 2002, 124: 6508
4Ngo H L, Hu A, Lin W. Tetrahedron Lett, 2005, 46: 595
5Pu L. Chem Rev, 1998, 98: 2405
6Fan Q H, Li Y M, Chan A S C. Chem Rev, 2002, 102: 3385
7Guernik S, Wolfson A, Herskowitz M, Greenspoon N, Geresh S. Chem Commun, 2001: 2314
8Brown R A, Pollet P, Mckoon E, Eckert C A, Liotta C L, Jessop P G. J Am Chem Soc, 2001, 123: 1254
9Zhu Y H, Carpenter K, Bun C C, Bahnmueller S, Chan P, Srid V S, Kee L W, Hawthorne M F. Angew Chem, Int Ed, 2003, 42: 3792
10Ngo H L, Hu A, Lin W. Chem Commun, 2003: 1912
11Hu A, Ngo H L, Lin W. Angew Chem, Int Ed, 2004, 43: 2501
12Lam K H, Xu L J, Feng L C, Ruan J W, Fan Q H, Chan A S C. Can J Chem, 2005, 83: 903
13Nasar K, Fache F, Lemaire M, Draye M, Béziat J C, Besson M, Galez P. J Mol Catal, 1994, 87: 107
14BKnnemann H, Braun G A. Chem Eur J, 1997, 3: 1200
15Zuo X, Liu H, Guo D, Yang X. Tetrahedron, 1999, 55: 7787
16Studer M, Blaser H U, Exner C. Adv Synth Catal, 2003, 345: 45
17Tamura M, Fujihara H. J Am Chem Soc, 2003, 125: 15742
18Jansat S, Gomez M, Philippot K, Muller G, Guiu E, Claver C, Castillon S, Chaudret B. J Am Chem Soc, 2004, 126: 1592
19Astruc D, Lu F, Aranzaes J R. Angew Chem, Int Ed, 2005, 44: 7852
20王金波, 明方永, 蒋维东, 樊光银, 刘德蓉, 陈华, 李贤均. 物理化学学报 (Wang J B, Ming F Y, Jiang W D, Fan G Y, Liu D R, Chen H, Li X J. Acta Phys-Chim Sin), 2007, 23: 1381
21刘德蓉, 熊伟, 杨朝芬, 王金波, 陈华, 李瑞祥, 李贤均. 物理化学学报 (Liu D R, Xiong W, Yang Ch F, Wang J B, Chen H, Li R X, Li X J. Acta Phys-Chim Sin), 2007, 23: 479
22姜和, 王金波, 熊伟, 贾云, 秦瑞香, 刘德蓉, 陈华. 物理化学学报 (Jiang H, Wang J B, Xiong W, Jia Y, Qin R X, Liu D R, Chen H. Acta Phys-Chim Sin), 2010, 26: 675
23王金波, 秦瑞香, 熊伟, 贾云, 刘德蓉, 陈华. 催化学报 (Wang J B, Qin R X, Xiong W, Jia Y, Liu D R, Chen H. Chin J Catal), 2010, 31: 273
24Wang J B, Qin R X, Fu H Y, Chen J, Feng J, Chen H, Li X J. Tetrahedron: Asymmetry, 2007, 18: 847
25Wang J B, Feng J, Qin R X, Fu H Y, Yuan M L, Chen H, Li X J. Tetrahedron: Asymmetry, 2007, 18: 1643
26Tang B, Xiong W, Liu D R, Jia Y, Wang J B, Chen H, Li X J. Tetrahedron: Asymmetry, 2008, 19: 1397
27Andrade C K Z, Alves L M. Curr Org Chem, 2005, 9: 195
28Chen J, Spear S K, Hunddleston J G, Rogers R D. Green Chem, 2005, 7: 64
29Reetz M T, Wiesenhofer W. Chem Commun, 2004: 2750
30Chandrasekhar S, Narsihmulu C, Reddy N R, Sultana S S. Tetrahedron Lett, 2004, 45: 4581
31Xu L J, Lam K H, Ji J X, Wu J, Fan Q H, Lo W H, Chan A S C. Chem Commun, 2005: 1390
32Zhou H F, Fan Q H, Tang W J, Xu L J, He Y M, Deng G J, Zhao L W, Gu L Q, Chan A S C. Adv Synth Catal, 2006, 348: 2172
33Zhou H F, Fan Q H, Huang Y Y, Wu L, He Y M, Tang W J, Gu L Q, Chan A S C. J Mol Catal A, 2007, 275: 47
34Zhou Z Q, Sun Y. React Kinet Mech Catal, 2010, 99: 391
35陈华, 刘海超, 黎耀忠, 程溥明, 李贤均. 分子催化 (Chen H, Liu H Ch, Li Y Zh, Chen F M, Li X J. J Mol Catal (China)), 1994, 8:124
36Thorpe T, Brown S M, Crosby J, Fitzjohn S, Muxworthy J P, Williams J M. Tetrahedron Lett, 2000, 41: 4503
37Ma Y P, Liu H, Chen L, Cui X, Zhu J, Deng J G. Org Lett, 2003, 5: 2103
38Pugin B, Studer M, Kuesters E, Sedelmeier G, Feng X. Adv Synth Catal, 2004, 346: 1481
39Laghmari M, Sinou D. J Mol Catal, 1991, 66: L15
40Sandoval C A, Ohkuma T, Munlz K, Noyori R. J Am Chem Soc, 2003, 125: 13490
41熊伟, 杨朝芬, 袁茂林, 陈华, 李贤均. 催化学报 (Xiong W, Yang Ch F, Yuan M L, Chen H, Li X J. Chin J Catal), 2005, 26: 1093
42Xiong W, Lin Q, Ma H X, Zheng H J, Chen H, Li X J. Tet-rahedron: Asymmetry, 2005, 16: 1959
43Noyori R, Ohkuma T. Angew Chem, Int Ed, 2001, 40: 40
44Kamaluddin A R, Faatz M, Alan A J, Morris R H. J Am Chem Soc, 2001, 123: 7473
45Liu D R, Xiong W, Fan G Y, Chen H, Li R X, Li X J. Appl Catal A, 2008, 339: 93

[1]	王露, 孙威, 刘超. 铜催化芳香醛和酮的氢硼化转化合成苄基硼酸酯类化合物[J]. 催化学报, 2018, 39(11): 1725-1729.
[2]	王涛, 吕元, 熊凯, 汪文龙, 张浩, 詹庄平, 姜政, 丁云杰. BINAP嵌入的多孔有机聚合物在多相不对称氢化反应中的作用[J]. 催化学报, 2017, 38(5): 890-898.
[3]	秦瑞香, 王金波, 熊伟, 冯建, 刘德蓉, 陈华. 聚乙二醇 400-水介质中水溶性钌膦二胺催化苄叉丙酮的不对称加氢反应[J]. 催化学报, 2012, 33(7): 1146-1153.
[4]	杨朝芬, 杨俊, 孙晓东, 朱艳琴, 王齐1, 陈华. (1S,2S)-1,2-二苯基乙二胺修饰 Ir/SiO₂ 催化苯乙酮及其衍生物不对称加氢[J]. 催化学报, 2012, 33(7): 1154-1160.
[5]	熊伟, 刘德蓉, 贾云, 秦瑞香, 邱会东, 王金波, 李贤均. L-脯氨酸修饰的 Ru-PPh₃/γ-Al₂O₃ 催化芳香酮不对称加氢反应[J]. 催化学报, 2011, 32(7): 1275-1279.
[6]	贺海峰;龚树文;刘丽君;崔庆新;尹汉东. SiO2 负载壳聚糖席夫碱钯催化剂催化芳香醛酮还原为芳香烃[J]. 催化学报, 2010, 31(7): 846-850.
[7]	王金波;秦瑞香;熊伟;贾云;刘德蓉;冯建;陈华. 水相中RuCl2(TPPTS)2-(S,S)-DPENDS催化苄叉丙酮的不对称加氢反应[J]. 催化学报, 2010, 31(3): 273-277.
[8]	彭宗海;马梦林;付海燕;陈华;李贤钧. 对烷氧基取代 MeO-BIPHEP 型手性双膦钌配合物催化 β-酮酸酯不对称加氢反应[J]. 催化学报, 2010, 31(2): 191-194.
[9]	陶国忠;卢冠忠;郭耘;王艳芹;郭杨龙;张志刚;刘晓晖;王筠松. 丙酮酸乙酯多相不对称催化加氢反应的初始过渡期研究[J]. 催化学报, 2009, 30(5): 391-395.
[10]	明方永;王金波;付海燕;陈骏;陈华;李贤均. 手性二胺修饰的Ru-TPP/γ-Al2O3催化苄叉丙酮不对称加氢反应[J]. 催化学报, 2007, 28(12): 1057-1061.
[11]	刘湘;方志杰;许建和. 酵母细胞催化芳香酮的不对称还原反应[J]. 催化学报, 2006, 27(1): 20-24.
[12]	熊伟;杨朝芬;袁茂林;陈华;李贤均. 水/有机两相体系中钌膦配合物催化苯乙酮及其衍生物的不对称加氢反应[J]. 催化学报, 2005, 26(12): 1093-1098.
[13]	夏涛;任其龙;吴平东. 2-氧代-4-苯基丁酸乙酯不对称加氢反应的动力学和机理探讨[J]. 催化学报, 2005, 26(11): 1011-1016.
[14]	黄艳轶;马红霞;熊伟;陈华;李贤均. Ru-(S)-BINAP/γ-Al2O3催化剂上苯乙酮及其衍生物的多相不对称加氢反应[J]. 催化学报, 2004, 25(12): 962-966.
[15]	马红霞;杨超;陈华;李贤均. 预处理和修饰条件对负载型铑纳米簇催化丙酮酸甲酯不对称加氢性能的影响[J]. 催化学报, 2003, 24(8): 619-623.

聚乙二醇-水介质中水溶性膦稳定的钌催化芳香酮的不对称加氢反应

Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Achiral Monophosphine TPPTS-Stabilized Ru in PEG-Water

PDF

可视化

被引次数

摘要/Abstract

引用本文

使用本文

扫码分享

参考文献

相关文章 15

编辑推荐

Metrics