多相双金属 Pt-Sn/γ-Al2O3 催化的胺 N-烷基化反应合成仲胺和叔胺

doi:10.3724/SP.J.1088.2012.11105

催化学报 ›› 2012, Vol. 33 ›› Issue (4): 717-722.DOI: 10.3724/SP.J.1088.2012.11105

多相双金属 Pt-Sn/γ-Al₂O₃ 催化的胺 N-烷基化反应合成仲胺和叔胺

赫巍, 何松波, 孙承林, 吴凯凯, 王连弟, 余正坤*

中国科学院大连化学物理研究所, 辽宁大连 116023

收稿日期:2011-11-07 修回日期:2011-11-28 出版日期:2012-04-13 发布日期:2015-09-09

Heterogeneous Bimetallic Pt-Sn/γ-Al₂O₃ Catalyzed N-Alkylation of Amines: Efficient Synthesis of Secondary and Tertiary Amines

HE Wei, HE Songbo, SUN Chenglin, WU Kaikai, WANG Liandi, YU Zhengkun*

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2011-11-07 Revised:2011-11-28 Online:2012-04-13 Published:2015-09-09

摘要/Abstract

摘要： 基于借氢策略、醇为烷基化试剂的胺的 N-烷基化反应是合成胺类化合物的绿色途径. 在无外加氢源条件下, 多相双金属 Pt-Sn/γ-Al₂O₃ 催化剂可高效催化醇为烷基化试剂的伯 (仲) 胺的 N-烷基化反应合成仲 (叔) 胺, 反应副产物为水与极少量亚胺. 催化体系的底物适应性好, 目标产物收率高; 催化剂可以循环使用, 具有潜在的工业化应用前景.

关键词: 铂, 锡, 氧化铝, 负载型催化剂, 借氢策略, 多相催化, N-烷基化, 胺, 醇

Abstract: N-Alkylation of amines with alcohols through a borrowing hydrogen strategy is a green route to amines. Heterogeneous bimetallic Pt-Sn/γ-Al₂O₃ catalyzed the reactions of primary (secondary) amines with alcohols in the absence of external hydrogen source, efficiently affording secondary (tertiary) amines with water and a small amount of imines as the by-products. Various functional groups in the substrates were tolerated in the catalytic system. The Pt-Sn/γ-Al₂O₃catalyst was easily recycled, suggesting its potential application in the production of secondary and tertiary amines.

Key words: platinum, tin, alumina, supported catalyst, borrowing hydrogen, heterogeneous catalysis, N-alkylation, amine, alcohol

赫巍, 何松波, 孙承林, 吴凯凯, 王连弟, 余正坤. 多相双金属 Pt-Sn/γ-Al₂O₃ 催化的胺 N-烷基化反应合成仲胺和叔胺[J]. 催化学报, 2012, 33(4): 717-722.

HE Wei, HE Song-Bo, SUN Cheng-Lin, WU Kai-Kai, WANG Lian-Di, YU Zheng-Kun. Heterogeneous Bimetallic Pt-Sn/γ-Al₂O₃ Catalyzed N-Alkylation of Amines: Efficient Synthesis of Secondary and Tertiary Amines[J]. Chinese Journal of Catalysis, 2012, 33(4): 717-722.

×
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.1088.2012.11105

https://www.cjcatal.com/CN/Y2012/V33/I4/717

参考文献

1 Brown B R. The Organic Chemistry of Aliphatic Nitrogen Compounds. New York: Oxford University Press, 1994
2 Salvatore R N, Yoon C H, Jung K W. Tetrahedron, 2001, 57: 7785
3 长谷川祥志, 西村彻, 广田敦史 (Chung Hasegawa, Toru Nishimura, Hirota Atsushi). CN 101 331 109. 2008
4 Hamid M H S A, Slatford P A, Williams J M J. Adv Synth Catal, 2007, 349: 1555
5 Watson A J A, Williams J M J. Science, 2010, 329: 635
6 Guillena G, Ramón D J, Yus M. Chem Rev, 2010, 110: 1611
7 Suzuki T. Chem Rev, 2011, 111: 1825
8 Hamid M H S A, Williams J M J. Tetrahedron Lett, 2007, 48: 8263
9 Grigg R, Mitchell T R B, Sutthivaiyakit S, Tongpenyai T, J Chem Soc, Chem Commun, 1981: 611
10 Watanabe Y, Tsuji Y, Ohsugi Y. Tetrahedron Lett, 1981, 22: 2667
11 Fujita K, Li Z, Ozeki N, Yamaguchi R. Tetrahedron Lett, 2003, 44: 2687
12 Fujita K-I, Yamaguchi R. Synlett, 2005, 4: 560
13 Fujita K-I, Enoki Y, Yamaguchi R. Org Synth, 2006, 83: 217
14 Fujita K-I, Enoki Y, Yamaguchi R. Tetrahedron, 2008, 64: 1943
15 Yamaguchi R, Kawagoe S, Asai C, Fujita K-I. Org Lett, 2008, 10: 181
16 Tillack A, Hollmann D, Michalik D, Beller M. Tetrahedron Lett, 2006, 47: 8881
17 Hollmann D, Tillack A, Michalk D, Jackstell R, Beller M. Chem Asian J, 2007, 2: 403
18 Bähn S, Imm S, Mevius K, Neubert L, Tillack A, Williams J M J, Beller M. Chem Eur J, 2010, 16: 3590
19 Hamid M H S A, Williams J M J. Chem Commun, 2007: 725
20 Hamid M H S A, Allen C L, Lamb G W, Maxwell A C, Maytum H C, Watson A J A, Williams J M J. J Am Chem Soc, 2009, 131: 1766
21 Saidi O, Blacker A J, Farah M M, Marsden S P, Williams J M J. Chem Commun, 2010: 1541
22 Waston A J A, Maxwell A C, Williams J M J. J Org Chem, 2011, 76: 2328
23 Shi F, Tse M K, Cui X J, Gördes D, Michalik D, Thurow K, Deng Y Q, Beller M. Angew Chem, Int Ed, 2009, 48: 5912
24 Fratt E F, Frazza E J. J Am Chem Soc, 1954, 76: 6174
25 He J L, Kim J W, Yamaguchi K, Mizuno N. Angew Chem, Int Ed, 2009, 48: 9888
26 Yamaguchi K, He J L, Oishi T, Mizuno N. Chem Eur J, 2010, 16: 7199
27 Shi F, Tse M K, Pohl M-M, Brückner A, Zhang S, Beller M. Angew Chem, Int Ed, 2007, 46: 8866
28 Shi F, Tse M K, Zhou S L, Pohi M M, Radnik J, Hübner S, Jähnisch K, Brückner A, Beller M. J Am Chem Soc, 2009, 131: 1775
29 Zhang Y, Qi X J, Cui X J, Shi F, Deng Y Q. Tetrahedron Lett, 2011, 52: 1334
30 Cui X J, Zhang Y, Shi F, Deng Y Q. Chem Eur J, 2011, 17: 1021
31 Cui X J, Shi F, Tse M K, Gördes D, Thurow K, Beller M, Deng Y Q. Adv Synth Catal, 2009, 351: 2949
32 Sun H, Su F Z, Ni J, Cao Y, He H Y, Fan K N. Angew Chem, Int Ed, 2009, 48: 4390
33 He L, Wang L C, Sun H, Ni J, Cao Y, He H Y, Fan K N. Angew Chem, Int Ed, 2009, 48: 9538
34 He L, Lou X B, Ni J, Liu Y M, Cao Y, He H Y, Fan K N. Chem Eur J, 2010, 16: 13965
35 Lou X B, He L, Qian Y, Liu Y M, Cao Y, Fan K N. Adv Synth Catal, 2011, 353: 281
36 Tang C H, He L, Liu Y M, Cao Y, He H Y, Fan K N. Chem Eur J, 2011, 17: 7172
37 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
38 Wang L D, He W, Wu K K, He S B, Sun C L, Yu Z K. Tet-rahedron Lett, 2011, 52: 7103
39 何松波, 赖玉龙, 毕文君, 杨旭, 荣欣, 孙承林. 催化学报 (He S B, Lai Y L, Bi W J, Yang X, Rong X, Sun Ch L. Chin J Catal), 2010, 31: 435
40 He S B, Sun C L, Bai Z W, Dai X H, Wang B. Appl Catal A, 2009, 356: 88

[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]	赵梦, 徐晶, 宋术岩, 张洪杰. 核壳/蛋黄壳纳米反应器用于串联催化[J]. 催化学报, 2023, 50(7): 83-108.
[12]	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.
[13]	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.
[14]	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.
[15]	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.

多相双金属 Pt-Sn/γ-Al₂O₃ 催化的胺 N-烷基化反应合成仲胺和叔胺

Heterogeneous Bimetallic Pt-Sn/γ-Al₂O₃ Catalyzed N-Alkylation of Amines: Efficient Synthesis of Secondary and Tertiary Amines

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