不同取代基铁咔咯配合物对苯乙烯的催化氧化

引用本文: 阳红, 邹怀波, 汪华华, 杨书宝, 章浩, 刘海洋. 不同取代基铁咔咯配合物对苯乙烯的催化氧化[J]. 无机化学学报, 2015, (5): 968-974. doi: 10.11862/CJIC.2015.141 shu

Citation: YANG Hong, WANG Hua-Hua, YANG Shu-Bao, ZHANG Hao, LIU Hai-Yang. Catalytic Styrene Oxidation by Iron Corroles Bearing Different Substituents[J]. Chinese Journal of Inorganic Chemistry, 2015, (5): 968-974. doi: 10.11862/CJIC.2015.141 shu

不同取代基铁咔咯配合物对苯乙烯的催化氧化

1.
华南理工大学化学系, 广州 510641

通讯作者: 刘海洋 cyduan@dlut.edu.cn

基金项目:
国家自然科学基金(No.21273027)资助项目。 (No.21273027)

摘要: 合成了4种具有不同推-拉电子强度取代基的铁咔咯配合物,并通过紫外,核磁,质谱等手段对化合物进行了表征。考察了在乙腈溶液中,以叔丁基过氧化氢(TBHP),亚碘酰苯(PhIO),双氧水(H₂O₂)为氧源时,4种不同取代基铁咔咯配合物对于苯乙烯的催化氧化效果,并考察了咪唑作为轴向配体时对反应的影响。结果表明,产物的产率与氧源,催化剂和轴向配体均有关。以TBHP为氧源时,苯甲醛为主要产物;以PhIO作为氧源时,主要产物则为环氧苯乙烷;而当氧源为H₂O₂时,4种铁咔咯均不能有效地催化苯乙烯氧化。使用不同的氧源时,4种铁咔咯展现不一样的催化活性顺序,其催化过程可能涉及自由基和高价态的Fe(Ⅴ)-oxo咔咯。铁咔咯能与咪唑形成1:2的配合物,在催化体系中加入咪唑后,在不同的氧源条件下,咪唑对于反应产物的分布影响不同。

关键词:

咔咯;铁;催化氧化;氧化剂;苯乙烯;轴向配体

English

Catalytic Styrene Oxidation by Iron Corroles Bearing Different Substituents

1.
Department of Chemistry, South China University of Technology, Guangzhou 510641, China

Corresponding author: 刘海洋 cyduan@dlut.edu.cn

Received Date: 29 September 2014
Fund Project:
国家自然科学基金(No.21273027)资助项目。

Abstract: Four meso-substituted iron(Ⅳ) corroles having different number of pentafluorophenylor phenyl groups were synthesized and characterized by UV-Vis, NMR and MS. The catalytic styrene oxidation by these iron corroles using tert-butyl hydroperoxide (TBHP), iodosylbenzene (PhIO), hydrogen peroxide(H₂O₂) in acetonitrile was investigated. The effect of imidazole as axial ligand on the catalytic oxidation was also examined. The results indicate that the yields of the products depend on oxidants, catalysts and axial ligand. For TBHP, benzaldehyde is the major product. Styrene epoxide is the major product when using PhIOoxidant. All iron(Ⅳ) corroles studied cannot effectively catalyze styrene oxidation by using H₂O₂. Four iron corroles exhibit different activity order when using different oxidants, and the catalytic process may involve free radical and Fe(Ⅴ)-oxocorrole species. The axial coordination of F₁₅C-Feby imidazole gives 1:2 complexes. Also, axial ligand imidazole has different effect on the oxidation product distribution when using different oxidants.

Key words:

corroles;iron;catalytic oxidation;oxidants;styrene;axial ligand

1. [1] Zhou X T, Tang Q H, Ji H B. Tetrahedron Lett., 2009,50 (47):6601-6605[1] Zhou X T, Tang Q H, Ji H B. Tetrahedron Lett., 2009,50 (47):6601-6605
2. [2] Rayati S, Jafarzadeh P, Zakavi S. Inorg. Chem. Commun., 2013,29:40-44[2] Rayati S, Jafarzadeh P, Zakavi S. Inorg. Chem. Commun., 2013,29:40-44
3. [3] Solati Z, HashemiM, Ebrahimi L. Catal. Lett., 2011,141(1): 163-167[3] Solati Z, HashemiM, Ebrahimi L. Catal. Lett., 2011,141(1): 163-167
4. [4] Guo C C, Song J X, Chen X B, et al. J. Mol. Catal. A: Chem., 2000,157(1/2):31-40[4] Guo C C, Song J X, Chen X B, et al. J. Mol. Catal. A: Chem., 2000,157(1/2):31-40
5. [5] Guo C C, Li H P, Xu J B. J. Catal., 1999,185(2):345-351[5] Guo C C, Li H P, Xu J B. J. Catal., 1999,185(2):345-351
6. [6] Ruppel J V, Gauthier T J, Snyder N L, et al. Org. Lett., 2009,11(11):2273-2276[6] Ruppel J V, Gauthier T J, Snyder N L, et al. Org. Lett., 2009,11(11):2273-2276
7. [7] Xu X, Lu H J, Ruppel J V, et al. J. Am. Chem. Soc., 2011, 133(39):15292-15295[7] Xu X, Lu H J, Ruppel J V, et al. J. Am. Chem. Soc., 2011, 133(39):15292-15295
8. [8] Vyas R, Gao G Y, Harden J D, et al. Org. Lett., 2004,6(12): 1907-1910[8] Vyas R, Gao G Y, Harden J D, et al. Org. Lett., 2004,6(12): 1907-1910
9. [9] Gao G Y, Jones J E, Vyas R, et al. J. Org. Chem., 2006,71 (17):6655-6658[9] Gao G Y, Jones J E, Vyas R, et al. J. Org. Chem., 2006,71 (17):6655-6658
10. [10] Gross Z, Gray H B. Adv. Synth. Catal., 2004,346(2/3):165-170[10] Gross Z, Gray H B. Adv. Synth. Catal., 2004,346(2/3):165-170
11. [11] Liu H Y, Lai T S, Yeung L L, et al. Org. Lett., 2003,5(5): 617-620[11] Liu H Y, Lai T S, Yeung L L, et al. Org. Lett., 2003,5(5): 617-620
12. [12] Dogutan D K, McGuire R J, Nocera D G. J. Am. Chem. Soc., 2011,133(24):9178-9180[12] Dogutan D K, McGuire R J, Nocera D G. J. Am. Chem. Soc., 2011,133(24):9178-9180
13. [13] Gross Z, Simkhovich L, Galili N. Chem. Commun., 1999,35, (7):599-600[13] Gross Z, Simkhovich L, Galili N. Chem. Commun., 1999,35, (7):599-600
14. [14] Simkhovich L, Mahammed A, Goldberg I, et al. Chem.-Eur. J., 2001,7(5):1041-1055[14] Simkhovich L, Mahammed A, Goldberg I, et al. Chem.-Eur. J., 2001,7(5):1041-1055
15. [15] Nakano K, Kobayahi T, Ohkawara T, et al. J. Am. Chem. Soc., 2013,135(23):8456-8459[15] Nakano K, Kobayahi T, Ohkawara T, et al. J. Am. Chem. Soc., 2013,135(23):8456-8459
16. [16] Liu H Y, Yam F, Xie Y T, et al. J. Am. Chem. Soc., 2009,131(36):12890-12891[16] Liu H Y, Yam F, Xie Y T, et al. J. Am. Chem. Soc., 2009,131(36):12890-12891
17. [17] Liu H Y, Mahmood M H R, Qiu S X, et al. Coord. Chem. Rev., 2013,257(7/8):1306-1333[17] Liu H Y, Mahmood M H R, Qiu S X, et al. Coord. Chem. Rev., 2013,257(7/8):1306-1333
18. [18] Liu H Y, Zhou H, Liu L Y, et al. Chem. Lett., 2007,36(2): 274-275[18] Liu H Y, Zhou H, Liu L Y, et al. Chem. Lett., 2007,36(2): 274-275
19. [19] Bose S, Pariyar A, Biswas A N, et al. Catal. Commun., 2011,12(6):446-449[19] Bose S, Pariyar A, Biswas A N, et al. Catal. Commun., 2011,12(6):446-449
20. [20] Biswas A N, Pariyar A, Bose S, et al. Catal. Commun., 2010,11(12):1008-1011[20] Biswas A N, Pariyar A, Bose S, et al. Catal. Commun., 2010,11(12):1008-1011
21. [21] Biswas A N, Das P, Agarwala A, et al. J. Mol. Catal. A: Chem., 2010,326(1/2):94-98[21] Biswas A N, Das P, Agarwala A, et al. J. Mol. Catal. A: Chem., 2010,326(1/2):94-98
22. [22] Pariyar A, Bose S, Biswas A N, et al. Catal. Commun., 2013,32:23-27[22] Pariyar A, Bose S, Biswas A N, et al. Catal. Commun., 2013,32:23-27
23. [23] Wang Q, Zhang Y, Yu L, et al. J. Porphyrins Phthalocyanines, 2014,18:316-325[23] Wang Q, Zhang Y, Yu L, et al. J. Porphyrins Phthalocyanines, 2014,18:316-325
24. [24] Peng S H, Mahmood M H R, Zou H B, et al. J. Mol.Catal. A: Chem., 2014,395:180-185[24] Peng S H, Mahmood M H R, Zou H B, et al. J. Mol.Catal. A: Chem., 2014,395:180-185
25. [25] CHEN Huan(陈欢), WEN Jin-Yan(闻金燕), YANG Hong (阳红), et al. ChineseJ. Inorg. Chem.(无机化学学报), 2014,30(7):1725-1732[25] CHEN Huan(陈欢), WEN Jin-Yan(闻金燕), YANG Hong (阳红), et al. ChineseJ. Inorg. Chem.(无机化学学报), 2014,30(7):1725-1732
26. [26] Liu H Y, Chen L, Yam F, et al. Chin. Chem. Lett., 2008,19 (8):1000-1003[26] Liu H Y, Chen L, Yam F, et al. Chin. Chem. Lett., 2008,19 (8):1000-1003
27. [27] LIAN Ping(练萍), LIU Hai-Yang(刘海洋), CHEN Ling (陈玲), et al. Chinese J. Inorg. Chem.(无机化学学报), 2009, 25(8):1420-1425[27] LIAN Ping(练萍), LIU Hai-Yang(刘海洋), CHEN Ling (陈玲), et al. Chinese J. Inorg. Chem.(无机化学学报), 2009, 25(8):1420-1425
28. [28] Kuwano T, Kurahashi T, Matsubara S. Chem. Lett., 2013,42 (10):1241-1243[28] Kuwano T, Kurahashi T, Matsubara S. Chem. Lett., 2013,42 (10):1241-1243
29. [29] Gross Z, Golubkov G, Simkhovich L. Angew. Chem. Int. Ed., 2000,39(22):4045-4047[29] Gross Z, Golubkov G, Simkhovich L. Angew. Chem. Int. Ed., 2000,39(22):4045-4047
30. [30] Wasbotten I, Ghosh A. Inorg. Chem., 2006,45(13):4910-4913[30] Wasbotten I, Ghosh A. Inorg. Chem., 2006,45(13):4910-4913
31. [31] Zhang R, Harischandra D N, Newcomb M. Chem. Eur. J., 2005,11(19):5713-5720[31] Zhang R, Harischandra D N, Newcomb M. Chem. Eur. J., 2005,11(19):5713-5720
32. [32] Zhang R, Newcomb M. Acc. Chem. Res., 2008,41(3):468-477 [33] Guedes A A, Santos A C M A, Assis M D, et al. Kinet. Catal., 2006,47(4):555-563[32] Zhang R, Newcomb M. Acc. Chem. Res., 2008,41(3):468-477 [33] Guedes A A, Santos A C M A, Assis M D, et al. Kinet. Catal., 2006,47(4):555-563
33. [34] LIU Jing-Jing(刘晶晶), WANG Hua-Hua(汪华华), YING Xiao(应晓), et al. Chem. J. Chinese Universities(高等化学学报), 2011,32(2):218-224[34] LIU Jing-Jing(刘晶晶), WANG Hua-Hua(汪华华), YING Xiao(应晓), et al. Chem. J. Chinese Universities(高等化学学报), 2011,32(2):218-224
34. [35] Cai S, Licoccia S, Walker F A. Inorg. Chem., 2001,40(23): 5795-5798[35] Cai S, Licoccia S, Walker F A. Inorg. Chem., 2001,40(23): 5795-5798
35. [36] Kurahashi S, Ikeue T, Sugimori T, et al. J. Porphyrins Phthalocyanines, 2012,16:518-529[36] Kurahashi S, Ikeue T, Sugimori T, et al. J. Porphyrins Phthalocyanines, 2012,16:518-529
36. [37] Miller J R, Dorough C D. J. Am. Chem. Soc., 1952,74(16): 3977-3981[37] Miller J R, Dorough C D. J. Am. Chem. Soc., 1952,74(16): 3977-3981

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

不同取代基铁咔咯配合物对苯乙烯的催化氧化

通讯作者: 刘海洋 cyduan@dlut.edu.cn

English

Catalytic Styrene Oxidation by Iron Corroles Bearing Different Substituents

Corresponding author: 刘海洋 cyduan@dlut.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

不同取代基铁咔咯配合物对苯乙烯的催化氧化

通讯作者: 刘海洋 cyduan@dlut.edu.cn

English

Catalytic Styrene Oxidation by Iron Corroles Bearing Different Substituents

Corresponding author: 刘海洋 cyduan@dlut.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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