温和条件下钒催化氧化胺、醇和胺直接合成亚胺

doi:10.1016/S1872-2067(14)60196-0

催化学报 ›› 2015, Vol. 36 ›› Issue (1): 19-23.DOI: 10.1016/S1872-2067(14)60196-0

温和条件下钒催化氧化胺、醇和胺直接合成亚胺

王连月^a, 陈波^a,b, 任兰会^a,b, 张恒耘^a, 吕迎^a, 高爽^a

a 中国科学院大连化学物理研究所洁净能源国家实验室(筹), 辽宁大连116023;
b 中国科学院大学, 北京100049

收稿日期:2014-06-20 修回日期:2014-07-16 出版日期:2014-12-31 发布日期:2014-12-31
通讯作者: 高爽
基金资助:
国家重点基础研究发展计划(973计划, 2009CB623505).

Vanadium catalyzed direct synthesis of imines from amines or alcohols and amines by an aerobic oxidative reaction under mild conditions

Lianyue Wang^a, Bo Chen^a,b, Lanhui Ren^a,b, Henyun Zhang^a, Ying Lü^a, Shuang Gao^a

a Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Received:2014-06-20 Revised:2014-07-16 Online:2014-12-31 Published:2014-12-31
Supported by:
This work was supported by the National Basic Research Program of China (973 Program, 2009CB623505).

摘要/Abstract

摘要：

开发了钒催化氧化胺、醇和胺直接合成亚胺催化体系, 无须额外的添加剂或促进剂, 空气作为环境友好的氧源, 温和条件下, 能高收率地得到各种对称和非对称亚胺, 并且催化剂非常容易制备和使用. 该催化体系对含杂原子亚胺的合成也非常有效.

关键词: 亚胺, 醇, 胺, 需氧氧化, 钒

Abstract:

The direct synthesis of imines from amines or alcohols and amines by vanadium catalyzed aerobic oxidation was developed. Without an additive or promoter, various symmetrical and unsymmetrical imines were obtained in good to excellent yields under mild conditions with air as an environmentally benign oxidant. The catalyst is very easy to prepare and use, and this catalytic system is also effective for the synthesis of heteroatom-containing imines.

Key words: Imine, Alcohol, Amine, Aerobic oxidation, Vanadium

王连月, 陈波, 任兰会, 张恒耘, 吕迎, 高爽. 温和条件下钒催化氧化胺、醇和胺直接合成亚胺[J]. 催化学报, 2015, 36(1): 19-23.

Lianyue Wang, Bo Chen, Lanhui Ren, Henyun Zhang, Ying Lü, Shuang Gao. Vanadium catalyzed direct synthesis of imines from amines or alcohols and amines by an aerobic oxidative reaction under mild conditions[J]. Chinese Journal of Catalysis, 2015, 36(1): 19-23.

×
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)60196-0

https://www.cjcatal.com/CN/Y2015/V36/I1/19

参考文献

[1] Murahashi S I. Angew Chem Int Ed, 1995, 34: 2443
[2] Gawronski J, Wascinska N, Gajewy J. Chem Rev, 2008, 108: 5227
[3] Adams J P. J Chem Soc, Perkin Trans 1, 2000: 125
[4] Layer R W. Chem Rev, 1963, 63: 489
[5] Gawronski J, Wascinska N, Gajewy J. Chem Rev, 2008, 108: 5227
[6] Taguchi K, Westheimer F H. J Org Chem, 1971, 36: 1570
[7] Das B, Ravikanth B, Laxminarayana K, Rao B V. J Mol Catal A, 2006, 253: 92
[8] Sun H, Su F Z, Ni J, Cao Y, He H Y, Fan K N. Angew Chem Int Ed, 2009, 48: 4390
[9] Kegnæs S, Mielby J, Mentzel U V, Christensen C H, Riisager A. Green Chem, 2010, 12: 1437
[10] Gnanaprakasam B, Zhang J, Milstein D. Angew Chem Int Ed, 2010, 49: 1468
[11] Su F Z, Mathew S C, Mohlmann L, Antonietti M, Wang X C, Blechert S. Angew Chem Int Ed, 2011, 50: 657
[12] Grirrane A, Corma A, Garcia H. J Catal, 2009, 264: 138
[13] Zhu B L, Angelici R J. Chem Commun, 2007: 2157
[14] So M H, Liu Y G, Ho C M, Che C M. Chem Asian J, 2009, 4: 1551
[15] Gunanathan C, Ben-David Y, Milstein D. Science, 2007, 317: 790
[16] Watson A J A, Williams J M J. Science, 2010, 329: 635
[17] Watson A J A, Maxwell A C, Williams J M J. Org Lett, 2009, 11: 2667
[18] Bala M, Verma P K, Kumar N, Sharma U, Singh B. Can J Chem, 2013, 91: 732
[19] Perez J M, Cano R, Yus M, Ramon D J. Eur J Org Chem, 2012, 2012: 4548
[20] Cano R, Ramon D J, Yus M. J Org Chem, 2011, 76: 5547
[21] Tang L, Sun H Y, Li Y F, Zha Z G, Wang Z Y. Green Chem, 2012, 14: 3423
[22] Reddy M M, Kumar M A, Swamy P, Naresh M, Srujana K, Satyanarayana L, Venugopal A, Narender N. Green Chem, 2013, 15: 3474
[23] Blackburn L, Taylor R J K. Org Lett, 2001, 3: 1637
[24] Yusubov M S, Chi K W, Park J Y, Karimov R, Zhdankin V V. Tetrahedron Lett, 2006, 47: 6305
[25] Kwon M S, Kim S, Park S, Bosco W, Chidrala R K, Park J. J Org Chem, 2009, 74: 2877
[26] Cui W J, Bao Z, Jia M L, Ao W L, Zhu H Y. RSC Adv, 2014, 4: 2601
[27] Furukawa S, Suga A, Komatsu T. Chem Commun, 2014, 50: 3277
[28] He W, Wang L D, Sun C L, Wu K K, He S B, Chen J P, Wu P, Yu Z K. Chem Eur J, 2011, 17: 13308
[29] Soule J F, Miyamura H, Kobayashi S. Chem Commun, 2013, 49: 355
[30] Zhang L L, Wang W T, Wang A Q, Cui Y T, Yang X F, Huang Y Q, Liu X Y, Liu W G, Son J Y, Oji H, Zhang T. Green Chem, 2013, 15: 2680
[31] Neeli C K P, Ganji S, Ganjala V S P, Kamaraju S R R, Burri D R. RSC Adv, 2014, 4: 14128
[32] Mielby J, Poreddy R, Engelbrekt C, Kengnæs S. Chin J Catal (催化学报), 2014, 35: 670
[33] Kim J W, He J L, Yamaguchi K, Mizuno N. Chem Lett, 2009, 38: 920
[34] Chem B, Li J, Dai W, Wang L Y, Gao S. Green Chem, 2014, 16: 3328
[35] Zhang E L, Tian H W, Xu S D, Yu X C, Xu Q. Org Lett, 2013, 15: 2704
[36] Kang Q, Zhang Y G. Green Chem, 2012, 14: 1016
[37] Huang B, Tian H W, Lin S S, Xie M H, Yu X C, Xu Q. Tetrahedron Lett, 2013, 54: 2861
[38] Tian H W, Yu X C, Li Q, Wang J X, Xu Q. Adv Synth Catal, 2012, 354: 2671
[39] Wang J Q, Lu S L, Cao X Q, Gu H W. Chem Commun, 2014, 50: 5637
[40] Jiang L, Jin L L, Tian H W, Yuan X Q, Yu X C, Xu Q. Chem Commun, 2011, 47: 10833
[41] Qiu X, Len C, Luque R, Li Y W. ChemSusChem, 2014, 7: 1684
[42] Punniyamurthy T, Velusamy S, Iqbal J. Chem Rev, 2005, 105: 2329
[43] Kodama S, Yoshida J, Nomoto A, Ueta Y, Yano S, Ueshima M, Ogawa A. Tetrahedron Lett, 2010, 51: 2450
[44] Hanson S K, Wu R L, Silks L A P. Org Lett, 2011, 13: 1908
[45] Hanson S K, Wu R L, Silks L A P. Angew Chem Int Ed, 2012, 51: 3410

温和条件下钒催化氧化胺、醇和胺直接合成亚胺

Vanadium catalyzed direct synthesis of imines from amines or alcohols and amines by an aerobic oxidative reaction under mild conditions

PDF

可视化

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]	高晖, 张恭, 程东方, 王永涛, 赵静, 李晓芝, 杜晓伟, 赵志坚, 王拓, 张鹏, 巩金龙. 构建Cu台阶位促进电催化CO₂还原制醇类化学品的研究[J]. 催化学报, 2023, 52(9): 187-195.
[2]	孙丽娟, 于晓慧, 唐丽永, 王伟康, 刘芹芹. 构建K₃PW₁₂O₄₀/CdS核壳S型异质结实现同步太阳能光催化分解水和选择性苯甲醇氧化反应[J]. 催化学报, 2023, 52(9): 164-175.
[3]	周双龙, 赵亮, 吕征, 代钰, 张琦, 赖建平, 王磊. 局部氧自由基的性质促进电催化乙醇选择性生成CO₂[J]. 催化学报, 2023, 52(9): 154-163.
[4]	张雯, 宋彩彩, 王嘉蔚, 蔡舒婷, 高梦语, 冯有祥, 鲁统部. 双向主客体作用促进水溶液中选择性光催化CO₂还原与醇氧化[J]. 催化学报, 2023, 52(9): 176-186.
[5]	Abhishek R. Varma, Bhushan S. Shrirame, Sunil K. Maity, Deepti Agrawal, Naglis Malys, Leonardo Rios-Solis, Gopalakrishnan Kumar, Vinod Kumar. C4二醇的发酵生产及其化学催化升级为高价值化学品的研究进展[J]. 催化学报, 2023, 52(9): 99-126.
[6]	乔蔚, 于立策, 常进法, 杨甫林, 冯立纲. MoSe₂纳米片耦合Pt纳米颗粒用于高效双功能催化甲醇辅助水电解制氢[J]. 催化学报, 2023, 51(8): 113-123.
[7]	程璐, 陈许宁, 胡培君, 曹宵鸣. 双氧水对于单核铜分子筛催化甲烷直接氧化制甲醇反应性能的利弊[J]. 催化学报, 2023, 51(8): 135-144.
[8]	孙利娟, 王伟康, 路平, 刘芹芹, 王乐乐, 唐华. 纳米高熵合金实现光催化剂肖特基势垒的调控用于光催化制氢与苯甲醇氧化耦合反应[J]. 催化学报, 2023, 51(8): 90-100.
[9]	孟帅奇, 李忠玉, 张鹏, Francisca Contreras, 季宇, Ulrich Schwaneberg. 深度学习指导的热裂褐藻角质酶工程用于促进PET解聚[J]. 催化学报, 2023, 50(7): 229-238.
[10]	安国庆, 张晓伟, 张灿阳, 高鸿毅, 刘斯奇, 秦耕, 齐辉, Jitti Kasemchainan, 张建伟, 王戈. 金属有机骨架基绿色催化剂在醇氧化反应中的研究应用[J]. 催化学报, 2023, 50(7): 126-174.
[11]	李慧珍, 陈艳蕾, 牛青, 王小凤, 刘哲源, 毕进红, 于岩, 李留义. 具有定向电荷传递能力的晶态线型聚酰亚胺材料驱动光催化CO₂还原[J]. 催化学报, 2023, 49(6): 152-159.
[12]	李显泉, 庞纪峰, 赵于嘉, 吴鹏飞, 于文广, 颜佩芳, 苏扬, 郑明远. Cu-MFI催化剂上Cu^δ⁺催化乙醇脱氢制乙醛[J]. 催化学报, 2023, 49(6): 91-101.
[13]	娄向西, 高璇, 刘钰, 褚名宇, 张丛洋, 邱盈华, 杨文秀, 曹暮寒, 王贵领, 张桥, 陈金星. 高效光热催化废旧聚酯塑料升级回收[J]. 催化学报, 2023, 49(6): 113-122.
[14]	赵志月, 蒋志伟, 黄一哲, Mebrouka Boubeche, Valentina G. Matveeva, Hector F. Garces, 罗惠霞, 严凯. 富空穴CoSi合金无溶剂无碱醇氧化[J]. 催化学报, 2023, 48(5): 175-184.
[15]	艾汉均, 赵丰乾, 吴小锋. 单电子还是双电子?反应底物决定的铁催化未活化烷基卤代物与胺、酰胺和吲哚的酰胺化反应机理[J]. 催化学报, 2023, 47(4): 121-128.