Citation: Shao-Lei Xie, Yong-Hai Hui, Xiang-Ju Long, Chang-Chun Wang, Zheng-Feng Xie. Aza-Michael addition reactions between nitroolefins and benzotriazole catalyzed by MCM-41 immobilized heteropoly acids in water[J]. Chinese Chemical Letters, ;2013, 24(01): 28-30. shu

Aza-Michael addition reactions between nitroolefins and benzotriazole catalyzed by MCM-41 immobilized heteropoly acids in water

  • Corresponding author: Yong-Hai Hui,  Zheng-Feng Xie, 
  • Received Date: 21 October 2012
    Available Online: 30 November 2012

  • MCM-41 supported heteropoly acids(HPAs)catalysts were synthesized,characterized and their catalytic activity was evaluated in an aza-Michael addition reaction between nitroolefins and benzotriazole in water at room temperature.50 wt%PW/MCM-41 showed the highest activity(up to 96%yield).The catalyst was used in six consecutive experiments without obvious loss of activity, confirming the success of the anchoring process and the catalyst stability.
  • 加载中
    1. [1]

      [1] T.Eicher,S.Hauptmann,The Chemistry of Heterocylces,2nd ed.,Wiley-VCH, New York,2003.

    2. [2]

      [2] M.G.M.Purwanto,K.Weisz,Non-natural nucleosides for the specific recognition of Watson-Crick base pairs,Curr.Org.Chem.7(2003)427-446.

    3. [3]

      [3] L.Yang,C.Xia,H.Huang,Chiral phosphoric acid catalyzed enantioselective aza-Michael addition of aromatic amines to nitroolefins,Chin.J.Catal.32(2011) 1573-1576.

    4. [4]

      [4] J.C.Anderson,G.J.Stepney,M.R.Mills,et al.,Enantioselective conjugate addition nitro-Mannich reactions:solvent controlled synthesis of acyclic anti- and syn-β-nitroamines with three contiguous stereocenters,J.Org.Chem.76(2011)1961-1971.

    5. [5]

      [5] R.Robiette,T.V.Tran,A.Cordi,B.Tinant,J.Marchand-Brynaert,A practical synthesis of 1,2-nitroamines by Michael addition of N-nucleophiles to nitroalk-enes,Synthesis 18(2010)3138-3142.

    6. [6]

      [6] J.Wang,H.Li,L.S.Zu,W.Wang,Enantioselective organocatalytic Michael addition reactions between N-heterocycles and nitroolefins,Org.Lett.8 (2006)1391-1394.

    7. [7]

      [7] J.Wang,W.T.Wang,X.H.Liu,et al.,Highly enantioselective direct Michael addition of 1H-benzotriazole to chalcones catalyzed by Sc(OTf)3/N,N'-dioxide complex,Eur.J.Org.Chem.44(2011)2039-2042.

    8. [8]

      [8] Q.L.Hua,C.Li,X.F.Wang,et al.,Enantioselective synthesis of chromans with a quaternary stereogenic centre through catalytic asymmetric cascade reactions, ACS Catal.1(2011)221-226.

    9. [9]

      [9] F.Hoffmann,M.Cornelius,J.Morell,M.Fröba,Silica-based mesoporous organic-inorganic hybrid materials,Angew.Chem.Int.Ed.45(2006)3216-3251.

    10. [10]

      [10] D.Carriazo,C.Domingo,C.Martin,V.Rives,PMo or PW heteropoly acids supported on MCM-41 silica nanoparticles:characterisation and FT-IR study of the adsorption of 2-butanol,J.Solid State Chem.181(2008)2046-2057.

    11. [11]

      [11] X.Sheng,Y.Zhou,Y.Zhang,M.Xue,Y.Duan,Immobilization of 12-tungstopho-sphoric acid on LaSBA-15 and its catalytic activity for alkylation of o-xylene with styrene,Chem.Eng.J.179(2012)295-301.

    12. [12]

      [12] A.N.Kharat,S.Moosavikia,B.T.Jahromi,A.Badiei,Liquid phase hydroxylation of benzene to phenol over vanadium substituted Keggin anion supported on amine functionalized SBA-15,J.Mol.Catal.A:Chem.348(2011)14-19.

    13. [13]

      [13] B.Li,W.Ma,C.Han,et al.,Preparation of MCM-41 incorporated with transition metal substituted polyoxometalate and its catalytic performance in esterification, Microporous Mesoporous Mater.156(2012)73-79.

    14. [14]

      [14] D.Enders,C.Wang,J.X.Liebich,Organocatalytic asymmetric aza-Michael addi-tions,Chem.Eur.J.15(2009)11058-11076.

  • 加载中
    1. [1]

      Yan-Li LiZhi-Ming LiKai-Kai WangXiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322

    2. [2]

      Jia-Cheng HouWei CaiHong-Tao JiLi-Juan OuWei-Min He . Recent advances in semi-heterogenous photocatalysis in organic synthesis. Chinese Chemical Letters, 2025, 36(2): 110469-. doi: 10.1016/j.cclet.2024.110469

    3. [3]

      Chuan-Zhi NiRuo-Ming LiFang-Qi ZhangQu-Ao-Wei LiYuan-Yuan ZhuJie ZengShuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862

    4. [4]

      . 第41卷第1期封面和目次. Acta Physico-Chimica Sinica, 2025, 41(1): -.

    5. [5]

      . 第41卷第3期封面和目次. Acta Physico-Chimica Sinica, 2025, 41(3): -.

    6. [6]

      . Cover and Table of Contents for Vol.41 No. 2. Acta Physico-Chimica Sinica, 2025, 41(2): -.

    7. [7]

      . Cover and Table of Contents for Vol.41 No. 4. Acta Physico-Chimica Sinica, 2025, 41(4): -.

    8. [8]

      Zhen DaiLinzhi TanYeyu SuKerui ZhaoYushun TianYu LiuTao Liu . Site-specific incorporation of reduction-controlled guest amino acids into proteins for cucurbituril recognition. Chinese Chemical Letters, 2024, 35(5): 109121-. doi: 10.1016/j.cclet.2023.109121

    9. [9]

      Hongmei YuBaoxi ZhangMeiju LiuCheng XingGuorong HeLi ZhangNingbo GongYang LuGuanhua Du . Theoretical and experimental cocrystal screening of temozolomide with a series of phenolic acids, promising cocrystal coformers. Chinese Chemical Letters, 2024, 35(5): 109032-. doi: 10.1016/j.cclet.2023.109032

    10. [10]

      Liangji ChenZhen YuanFudong FengXin ZhouZhile XiongWuji WeiHao ZhangBanglin ChenShengchang XiangZhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344

    11. [11]

      Yanjing LiJiayin LiYuqi ChangYunfeng LinLei Sui . Tetrahedral framework nucleic acids promote the proliferation and differentiation potential of diabetic bone marrow mesenchymal stem cell. Chinese Chemical Letters, 2024, 35(9): 109414-. doi: 10.1016/j.cclet.2023.109414

    12. [12]

      Xiang HuangDongzhen XuYang LiuXia HuangYangfan WuDongmei FangBing XiaWei JiaoJian LiaoMin Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665

    13. [13]

      Qian RenXue DaiRan CenYang LuoMingyang LiZiyun ZhangQinghong BaiZhu TaoXin Xiao . A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution. Chinese Chemical Letters, 2024, 35(12): 110022-. doi: 10.1016/j.cclet.2024.110022

    14. [14]

      Min-Hang ZhouJun JiangWei-Min He . EDA-complexes-enabled photochemical synthesis of α-amino acids with imines and tetrabutylammonium oxalate. Chinese Chemical Letters, 2025, 36(1): 110446-. doi: 10.1016/j.cclet.2024.110446

    15. [15]

      Xinyi LuoKe WangYingying XueXiaobao CaoJianhua ZhouJiasi Wang . Digital PCR-free technologies for absolute quantitation of nucleic acids at single-molecule level. Chinese Chemical Letters, 2025, 36(2): 109924-. doi: 10.1016/j.cclet.2024.109924

    16. [16]

      Pengfei ZhangQingxue MaZhiwei JiangXiaohua XuZhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361

    17. [17]

      Fanxin Kong Hongzhi Wang Huimei Duan . Inhibition effect of sulfation on Pt/TiO2 catalysts in methane combustion. Chinese Journal of Structural Chemistry, 2024, 43(5): 100287-100287. doi: 10.1016/j.cjsc.2024.100287

    18. [18]

      Xianxu ChuLu WangJunru LiHui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105

    19. [19]

      Pingfan ZhangShihuan HongNing SongZhonghui HanFei GeGang DaiHongjun DongChunmei Li . Alloy as advanced catalysts for electrocatalysis: From materials design to applications. Chinese Chemical Letters, 2024, 35(6): 109073-. doi: 10.1016/j.cclet.2023.109073

    20. [20]

      Ting WangXin YuYaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320

Metrics
  • PDF Downloads(0)
  • Abstract views(806)
  • HTML views(11)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return