V@CN催化的芳烃的氧气羟基化反应

doi:10.1016/S1872-2067(14)60319-3

催化学报 ›› 2015, Vol. 36 ›› Issue (7): 1086-1092.DOI: 10.1016/S1872-2067(14)60319-3

V@CN催化的芳烃的氧气羟基化反应

李岩, 李冰, 陈婷, 周志成, 王军, 黄军

南京工业大学材料化学工程国家重点实验室, 江苏南京210009

收稿日期:2015-01-15 修回日期:2015-02-16 出版日期:2015-06-12 发布日期:2015-07-30
通讯作者: 黄军, 电话: (025)83172261; 电子信箱: junhuang@njtech.edu.cn
基金资助:
国家自然科学基金(21136005); 国家高技术研究发展计划(863计划, 2012AA03A606); 江苏高校优势学科建设工程(PAPD, 38701001).

Direct hydroxylation of arenes with O₂ catalyzed by V@CN catalyst

Yan Li, Bing Li, Ting Chen, Zhicheng Zhou, Jun Wang, Jun Huang

State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing Tech University, Nanjing 210009, Jiangsu, China

Received:2015-01-15 Revised:2015-02-16 Online:2015-06-12 Published:2015-07-30
Supported by:
This work was supported by the National Natural Science of Foundation of China (21136005), the National High Technology Research and Development Program of China (863 Program, 2012AA03A606), and the Project of Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD, 38701001).

摘要/Abstract

摘要：

制备了V@CN催化剂, 并用于氧气条件下芳烃的直接羟基化反应. 结果表明, 在V@CN催化剂作用下, 带有不同吸电子基团(CN, NO₂, COOH, CF₃和COCH₃)的芳烃均可被O₂氧化得到相应的酚, 产率中等. 含有卤素(F, Cl和Br)的芳烃也可在该催化体系作用下转化为相应的酚.

关键词: 羟基化, 钒催化剂, 芳烃, 氧气, 石墨相氮化碳

Abstract:

A vanadium doped graphitic carbon nitride catalyst has been prepared and used for the direct hydroxylation of arenes with O₂. Substituted arenes with electron-withdrawing groups such as CN, NO₂, COOH, CF₃, and COCH₃ were oxygenated to the corresponding phenols in moderate yields. The catalyst also proved applicable for the hydroxylation of aromatic halides (F, Cl, and Br) with O₂.

Key words: Hydroxylation, Vanadium, Arene, Oxygen, Graphitic carbon nitride

李岩, 李冰, 陈婷, 周志成, 王军, 黄军. V@CN催化的芳烃的氧气羟基化反应[J]. 催化学报, 2015, 36(7): 1086-1092.

Yan Li, Bing Li, Ting Chen, Zhicheng Zhou, Jun Wang, Jun Huang. Direct hydroxylation of arenes with O₂ catalyzed by V@CN catalyst[J]. Chinese Journal of Catalysis, 2015, 36(7): 1086-1092.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(14)60319-3

https://www.cjcatal.com/CN/Y2015/V36/I7/1086

参考文献

[1] Fiege H, Voges H W, Hamamoto T, Umemura S, Iwata T, Miki H, Fujita Y, Buysch H J, Garbe D, Paulus W. In: Ullmann F. Ullmann’s Encyclopedia of Industrial Chemistry. 6th Ed. Weinheim: Wiley- VCH, 2012. 521
[2] Laufer W, Hoelderich W F. Chem Commun, 2002: 1684
[3] Tatsumi T, Yuasa K, Tominaga H. J Chem Soc, Chem Commun, 1992: 1446
[4] Bianchi D, D’Aloisio R, Bortolo R, Ricci M. Appl Catal A, 2007, 327: 295
[5] Wang X Q, Wu J P, Zhao M W, Lü Y F, Li G Y, Hu C W. J Phys Chem C, 2009, 113: 14270
[6] Bartoli J F, Mouries-Mansuy V, Le Barch-Ozette K, Palacio M, Battioni P, Mansuy D. Chem Commun, 2000: 827
[7] Mori K, Kagohara K, Yamashita H. J Phys Chem C, 2008, 112: 2593
[8] Roy P, Dhara K, Manassero M, Banerjee P. Eur J Inorg Chem, 2008, 4404
[9] Tandon P K, Baboo R, Singh A K, Purwar G, Purwar M. Appl Organomet Chem, 2005, 19: 1079
[10] Marsella A, Agapakis S, Pinna F, Strukul G. Organometallics, 1992, 11: 3578
[11] Gao F X, Hua R M. Appl Catal A, 2004, 270: 223
[12] Raja R, Thomas J M, Dreyer V. Catal Lett, 2006, 110: 179
[13] Pirutko L V, Chernyavsky V S, Uriarte A K, Panov G I. Appl Catal A, 2002, 227: 143
[14] Costine A, O’Sullivan T, Hodnett B K. Catal Today, 2005, 99: 199
[15] Niwa S I, Eswaramoorthy M, Nair J, Raj A, Itoh N, Shoji H, Namba T, Mizukami F. Science, 2002, 295: 105
[16] Tani M, Sakamoto T, Mita S, Sakaguchi S, Ishii Y. Angew Chem Int Ed, 2005, 44: 2586
[17] Bolm C. Coord Chem Rev, 2003, 237: 245
[18] Shul’pin G B, Lachter E R. J Mol Catal A, 2003, 197: 65
[19] de la Cruz M H C, Kozlov Y N, Lachter E R, Shul’pin G B. New J Chem, 2003, 27: 634
[20] Yin C X, Finke R G. J Am Chem Soc, 2005, 127: 9003
[21] Zhao L N, Dong Y L, Zhan X L, Cheng Y, Zhu Y J, Yuan F L, Fu H G. Catal Lett, 2012, 142: 619
[22] Gu Y Y, Zhao X H, Zhang G R, Ding H M, Shan Y K. Appl Catal A, 2007, 328: 150
[23] Kanzaki H, Kitamura T, Hamada R, Nishiyama S, Tsuruya S. J Mol Catal A, 2004, 208: 203
[24] Ichihashi Y, Taniguchi T, Amano H, Atsumi T, Nishiyama S, Tsuruya S. Top Catal, 2008, 47: 98
[25] Zhou C J, Wang J, Leng Y, Ge H Q. Catal Lett, 2010, 135: 120
[26] Chen J Q, Gao S, Li J, Lü Y. Chin J Catal (陈佳琦, 高爽, 李军, 吕迎. 催化学报), 2011, 32: 1446
[27] Kamata K, Yamaura T, Mizuno N. Angew Chem Int Ed, 2012, 51: 7275
[28] Yan Y P, Feng P, Zheng Q Z, Liang Y F, Lu J F, Cui Y X, Jiao N. Angew Chem Int Ed, 2013, 52: 5827
[29] Zhang Y H, Yu J Q. J Am Chen Soc, 2009, 131: 14654
[30] Liu Q, Wu P, Yang Y H, Zeng Z Q, Liu J, Yi H, Lei A W. Angew Chem Int Ed, 2012, 51: 4666
[31] Khenkin A M, Weiner L, Neumann R. J Am Chem Soc, 2005, 127: 9988
[32] Li Y, Wang Z, Chen R Z, Wang Y, Xing W H, Wang J, Huang J. Catal Commun, 2014, 55: 34
[33] Li Y, Li B, Geng L F, Wang J, Wang Y, Huang J. Catal Lett, DOI: 10.1007/s10562-015-1478-7
[34] Wang X C, Chen X F, Thomas A, Fu X Z, Antonietti M. Adv Mater, 2009, 21: 1609
[35] Wang Y, Wang X C, Antonietti M. Angew Chem Int Ed, 2012, 51: 68
[36] Wang Y, Li H R, Yao J, Wang X C, Antonietti M. Chem Sci, 2011, 2: 446
[37] Gao Y J, Hu G, Zhong J, Shi Z J, Zhu Y S, Su D S, Wang J G, Bao X H, Ma D. Angew Chem Int Ed, 2013, 52: 2109
[38] Li X H, Wang X C, Antonietti M. ACS Catal, 2012, 2: 2082
[39] Li X H, Chen J S, Wang X C, Sun J H, Antonietti M. J Am Chem Soc, 2011, 133: 8074
[40] Goettmann F, Fischer A, Antonietti M, Thomas A. Angew Chem Int Ed, 2006, 45: 4467
[41] Ding Z X, Chen X F, Antonietti M, Wang X C. ChemSusChem, 2011, 4: 274
[42] Chen X F, Zhang J S, Fu X Z, Antonietti M, Wang X C. J Am Chem Soc, 2009, 131: 11658
[43] Ding G D, Wang W T, Jiang T, Han B X, Fan H L, Yang G Y. ChemCatChem, 2013, 5: 192
[44] Long Z Y, Zhou Y, Chen G J, Ge W L, Wang J. Sci Rep, 2014, 4: 3651
[45] Dong F, Wu L W, Sun Y J, Fu M, Wu Z B, Lee S C. J Mater Chem, 2011, 21: 15171
[46] Thomas A, Fischer A, Goettmann F, Antonietti M, Mueller J O, Schlogl R, Carlsson J M. J Mater Chem, 2008, 18: 4893
[47] Chen X, Zhao B T, Cai Y, Tade M O, Shao Z P. Nanoscale, 2013, 5: 12589

V@CN催化的芳烃的氧气羟基化反应

Direct hydroxylation of arenes with O₂ catalyzed by V@CN catalyst

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

[1]	危长城, 张雯娜, 杨阔, 柏秀, 徐舒涛, 李金哲, 刘中民. CO₂作为化学品原料的高效利用途径: 与烷烃耦合反应[J]. 催化学报, 2023, 47(4): 138-149.
[2]	池海波, 王旺银, 马江平, 段睿智, 丁春梅, 宋睿, 李灿. 光电催化脱氟-氧化过程实现氟芳烃污染物的高效矿化[J]. 催化学报, 2023, 55(12): 171-181.
[3]	桂清文, 滕帆, 喻鹏, 吴一帆, 农志彬, 杨龙汐, 陈祥, 阳天宝, 何卫民. 可见光诱导Z型V₂O₅/g-C₃N₄异质结催化未活化烯烃串联反应[J]. 催化学报, 2023, 44(1): 111-116.
[4]	伯知豫, 颜思顺, 高田宇, 宋磊, 冉川昆, 何轶, 章炜, 曹光梅, 余达刚. 可见光催化二氧化碳参与多氟芳烃的选择性C-F键羧基化[J]. 催化学报, 2022, 43(9): 2388-2394.
[5]	何杰, 王选东, 金尚彬, 刘兆清, 朱明山. 二维非金属的石墨相氮化碳/共价三嗪骨架异质结构材料用于高效和高选择性光催化二氧化碳还原[J]. 催化学报, 2022, 43(5): 1306-1315.
[6]	吴鹏, 张锦岩, 陈倩倩, 彭炜, 王斌举. 对比生物体系以及合成体系中单核铜氧物种对碳氢键和氧氢键活化的理论研究展望[J]. 催化学报, 2022, 43(4): 913-927.
[7]	谭亚其, 尹艳丽, 曹珊珊, 赵筱薇, 渠桂荣, 江智勇. 氢原子转移与手性氢键协同催化共轭加成—不对称质子化构建氮杂芳烃α-三级立体中心[J]. 催化学报, 2022, 43(3): 558-563.
[8]	于晓慧, 苏海伟, 邹建平, 刘芹芹, 王乐乐, 唐华. 利用掺杂诱导的金属-N活性位点和带隙调控提升石墨相氮化碳的光催化产氢性能[J]. 催化学报, 2022, 43(2): 421-432.
[9]	黄婷, 陈佳琪, 张莉莉, Alireza Khataee, 韩巧凤, 刘孝恒, 孙敬文, 朱俊武, 潘书刚, 汪信, 付永胜. 前驱体改性法制备薄层多孔富氨基的石墨相氮化碳用于光催化降解RhB和光催化制氢[J]. 催化学报, 2022, 43(2): 497-506.
[10]	张敏, 李云锋, 常薇, 朱炜, 张洛红, 金仁喜, 邢艳. 具有增强电荷转移驱动的磺酸基功能化g-C₃N₄光催化剂的设计合成及应用[J]. 催化学报, 2022, 43(2): 526-535.
[11]	张瑜, 张玲, 曾滴, 王文婧, 王举雪, 王伟民, 王文中. 富氧石墨相氮化碳在磷酸钠溶液中高效光催化合成过氧化氢[J]. 催化学报, 2022, 43(10): 2690-2698.
[12]	田栋, 孙鑫, 曹珊珊, 王二萌, 尹艳丽, 赵筱薇, 江智勇. 乙烯基氮杂芳烃参与的不对称分子间[2 + 2]光环加成反应[J]. 催化学报, 2022, 43(10): 2732-2742.
[13]	俞浩然, 刘丹旭, 王恒屹, 于海爽, 闫青云, 嵇家辉, 张金龙, 邢明阳. CoP助催化光芬顿中单线态氧协同表面吸附羟基自由基降解苯酚[J]. 催化学报, 2022, 43(10): 2678-2689.
[14]	李访, 岳晓阳, 周海平, 范佳杰, 向全军. 氰基修饰石墨相氮化碳构建高效的活性位点用于光催化还原CO₂[J]. 催化学报, 2021, 42(9): 1608-1616.
[15]	陈之旸, 倪友明, 文富利, 周子乔, 朱文良, 刘中民. 金属氧化物催化剂上合成气转化中羧酸盐物种促进芳烃的生成[J]. 催化学报, 2021, 42(5): 835-843.

V@CN催化的芳烃的氧气羟基化反应

Direct hydroxylation of arenes with O2 catalyzed by V@CN catalyst

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

Direct hydroxylation of arenes with O₂ catalyzed by V@CN catalyst