Citation: Farhad Shirini, Seyyed Vahid Atghia, Mojtaba Ghazi Jirdehi. Nanocrystalline TiO2-HClO4:A novel,efficient and recyclable catalyst for the chemoselective N-Boc protection of amines under solvent-free conditions[J]. Chinese Chemical Letters, ;2013, 24(01): 34-36. shu

Nanocrystalline TiO2-HClO4:A novel,efficient and recyclable catalyst for the chemoselective N-Boc protection of amines under solvent-free conditions

  • Corresponding author: Farhad Shirini, 
  • Received Date: 5 June 2012
    Available Online: 23 September 2012

  • Nanocrystalline TiO2-HClO4,as newly reported catalyst,has been used as an efficient and reusable catalyst for the chemoselective N-Boc protection of amines.The clean,mild acidity condition, quantitative yields of products,short reaction time and low reaction temperature are attractive features of this reaction.In practice,this method is a combination of a satisfactory synthesis and more significantly easy product isolation and purification.
  • 加载中
    1. [1]

      [1] T.W.Greene,P.G.M.Wuts,Protecting Group in Organic Synthesis,John Wiley and Sons,New York,1999.

    2. [2]

      [2] P.J.Kocienski,Protecting Groups,Georg Thieme,New York,2000.

    3. [3]

      [3] M.J.Burk,J.G.Allen,A mild amide to carbamate transformation,J.Org.Chem.62 (1997)7054-7057.

    4. [4]

      [4] Y.Basel,A.Hassner,Di-tert-butyl dicarbonate and 4-(dimethylamino)-pyridine revisited.Their reactions with amines and alcohols,J.Org.Chem.65(2000)6368-6380.

    5. [5]

      [5] R.B.Harris,I.B.Wilson,Synthesis of tert-butyl aminocarbonate,a new type of compound that can be used to acylate amines,Tetrahedron Lett.24(1983)231-232.

    6. [6]

      [6] R.Varala,S.Nuvula,S.R.Adapa,Molecular iodine-catalyzed facile procedure for N-Boc protection of amines,J.Org.Chem.71(2006)8283-8286.

    7. [7]

      [7] R.K.Pandey,S.P.Ragade,K.Upadhyay,M.K.Dongare,P.Kumar,A facile procedure for tert-butoxycarbonylation of amines promoted by yttria-zirconia based strong Lewis acid catalyst,Arkivoc VⅡ(2002)28-33.

    8. [8]

      [8] G.V.M.Sharma,J.J.Reddy,P.S.Lakshmi,P.R.Krishna,Rapid and facile Lewis acid catalysed Boc protection of amines,Tetrahedron Lett.45(2004)6963-6965.

    9. [9]

      [9] G.Bartoli,M.Bosco,M.Locatelli,et al.,Synthesis of N-functionalized 3,4-O-carboranylenepiperidines as potential boron neutron capture therapy agents, Synlett 10(2004)1794-1798.

    10. [10]

      [10] A.Heydari,S.E.Hosseini,Lithium perchlorate-catalyzed Boc protection of amines and amine derivatives,Adv.Synth.Catal.347(2005)1929-1931.

    11. [11]

      [11] S.Chankeshwara,A.K.Chakraborti,Montmorillonite K10 and montmorillonite KSF as new and reusable catalysts for conversion of amines to N-tert-butylcar-bamates,J.Mol.Catal.A:Chem.253(2006)198-202.

    12. [12]

      [12] N.Suryakiran,P.Prabhakar,S.T.Reddy,K.Rajesh,Y.Venkateswarlu,Facile N-tert-butoxycarbonylation of amines using La(NO3)3á6H2O as a mild and efficient catalyst under solvent-free conditions,Tetrahedron Lett.47(2006)8039-8042.

    13. [13]

      [13] F.Shirini,M.A.Zolfigol,M.Abedini,Saccharin sulfonic acid catalyzed N-Boc protection of amines and formation of tert-butyl ethers from alcohols,J.Iran. Chem.Soc.7(2010)603-607.

    14. [14]

      [14] F.Shirini,M.Mamaghani,S.V.Atghia,Sulfonic acid-functionalized ordered nano-porous Na+-montmorillonite(SANM):a novel,efficient and recyclable catalyst for the chemoselective N-Boc protection of amines in solventless media,Catal. Commun.12(2011)1088-1094.

    15. [15]

      [15] F.Shirini,N.Ghaffari Khaligh,Succinimide sulfonic acid(SuSA):an efficient and recyclable catalyst for the chemoselective N-Boc protection of amines,Monatsh. Chem.143(2012)631-635.

    16. [16]

      [16] J.Akbari,A.Heydari,L.Mámani,S.H.C.R.Hosseini,Protic ionic liquid[TMG] [Ac] as an efficient,homogeneous and recyclable catalyst for Boc protection of amines,C. R.Chim.13(2010)544-547.

    17. [17]

      [17] B.Das,K.Venkateswarlu,M.Krishnaiah,H.Holla,A highly chemoselective Boc protection of amines using sulfonic-acid-functionalized silica as an effi-cient heterogeneous recyclable catalyst,Tetrahedron Lett.47(2006)7551-7556.

    18. [18]

      [18] A.Heydari,R.K.Shiroodi,H.Hamidi,M.Esfandyari,M.Pourayoubi,N-tert-butox-ycarbonylation of amines using H3PW12O40 as an efficient heterogeneous and recyclable catalyst,Tetrahedron Lett.48(2007)5865-5868.

    19. [19]

      [19] S.Khaksar,S.M.Vahdat,M.Tajbakhsh,F.Jahani,A.Heydari,Thioglycoluril as a highly efficient,recyclable and novel organocatalyst for N-Boc protection of amines,Tetrahedron Lett.51(2010)6388-6391.

    20. [20]

      [20] S.Khaksar,A.Heydari,M.Tajbakhsh,S.M.Vahdat,Hydrogen bond catalyzed chemoselective N-tert-butoxycarbonylation of amines,Tetrahedron Lett.49 (2008)3527-3529.

    21. [21]

      [21] D.J.Upadhyaya,A.Barge,R.Stefania,G.Cravotto,Efficient,solventless N-Boc protection of amines carried out at room temperature using sulfamic acid as recyclable catalyst,Tetrahedron Lett.48(2007)8318-8322.

    22. [22]

      [22] J.C.Schumacher,Perchlorates—Their Properties,Manufacture and Uses,ACS Monograph Series,Reinhold,New York,1960.

    23. [23]

      [23] J.Long,Perchlorate safety:reconciling inorganic and organic guidelines,Chem. Health Saf.9(2002)12-18.

    24. [24]

      [24] F.Shirini,S.V.Atghia,M.Ghazi Jirdehi,Nanocrystalline TiO2-HClO4 as a new, efficient and recyclable catalyst for the chemoselective trimethylsilylation of alcohols,phenols and deprotection of silyl ethers,Catal.Commun.18(2012)5-10.

    25. [25]

      [25] A.K.Chakraborti,S.V.Chankeshwara,HClO4-SiO2 as a new,highly efficient, inexpensive and reusable catalyst for N-tert-butoxy-carbonylation of amines, Org.Biomol.Chem.4(2006)2769-2771.

  • 加载中
    1. [1]

      Jun ZhangZhiyao ZhengCan Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160

    2. [2]

      Jingjie Tang Luying Xie Jiayu Liu Shangyu Shi Xinyu Sun Jiayang Lin Qikun Yang Chuan'ang Yu Zecheng Wang Yingying Wang Zengyang Xie . Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University. University Chemistry, 2024, 39(3): 316-326. doi: 10.3866/PKU.DXHX202309091

    3. [3]

      Wen-Tao OuyangJun JiangYan-Fang JiangTing LiYuan-Yuan LiuHong-Tao JiLi-Juan OuWei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038

    4. [4]

      Meiling XuXinyang LiPengyuan LiuJunjun LiuXiao HanGuodong ChaiShuangling ZhongBai YangLiying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860

    5. [5]

      Yuan ZhangShenghao GongA.R. Mahammed ShaheerRong CaoTianfu Liu . Plasmon-enhanced photocatalytic oxidative coupling of amines in the air using a delicate Ag nanowire@NH2-UiO-66 core-shell nanostructures. Chinese Chemical Letters, 2024, 35(4): 108587-. doi: 10.1016/j.cclet.2023.108587

    6. [6]

      Wenxuan YangLong ShangXiaomeng LiuSihan ZhangHaixia LiZhenhua YanJun Chen . Ultrafast synthesis of nanocrystalline spinel oxides by Joule-heating method. Chinese Chemical Letters, 2024, 35(11): 109501-. doi: 10.1016/j.cclet.2024.109501

    7. [7]

      Xin JiangHan JiangYimin TangHuizhu ZhangLibin YangXiuwen WangBing Zhao . g-C3N4/TiO2-X heterojunction with high-efficiency carrier separation and multiple charge transfer paths for ultrasensitive SERS sensing. Chinese Chemical Letters, 2024, 35(10): 109415-. doi: 10.1016/j.cclet.2023.109415

    8. [8]

      Hai-Yang SongJun JiangYu-Hang SongMin-Hang ZhouChao WuXiang ChenWei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246

    9. [9]

      Zihao WangJing XueZhicui SongJianxiong XingAijun ZhouJianmin MaJingze Li . Li-Zn alloy patch for defect-free polymer interface film enables excellent protection effect towards stable Li metal anode. Chinese Chemical Letters, 2024, 35(10): 109489-. doi: 10.1016/j.cclet.2024.109489

    10. [10]

      Fei ZHOUXiaolin JIA . Co3O4/TiO2 composite photocatalyst: Preparation and synergistic degradation performance of toluene. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2232-2240. doi: 10.11862/CJIC.20240236

    11. [11]

      Xuejiao Wang Suiying Dong Kezhen Qi Vadim Popkov Xianglin Xiang . Photocatalytic CO2 Reduction by Modified g-C3N4. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005

    12. [12]

      Liang Ma Zhou Li Zhiqiang Jiang Xiaofeng Wu Shixin Chang Sónia A. C. Carabineiro Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416

    13. [13]

      Jiajun WangGuolin YiShengling GuoJianing WangShujuan LiKe XuWeiyi WangShulai Lei . Computational design of bimetallic TM2@g-C9N4 electrocatalysts for enhanced CO reduction toward C2 products. Chinese Chemical Letters, 2024, 35(7): 109050-. doi: 10.1016/j.cclet.2023.109050

    14. [14]

      Hui LiYanxing QiJia ChenJuanjuan WangMin YangHongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO2 and selectivity over N2 and CH4. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659

    15. [15]

      Xing Xiao Yunling Jia Wanyu Hong Yuqing He Yanjun Wang Lizhi Zhao Huiqin An Zhen Yin . Sulfur-defective ZnIn2S4 nanosheets decorated by TiO2 nanosheets with exposed {001} facets to accelerate charge transfer for efficient photocatalytic hydrogen evolution. Chinese Journal of Structural Chemistry, 2024, 43(12): 100474-100474. doi: 10.1016/j.cjsc.2024.100474

    16. [16]

      Shuangxi LiHuijun YuTianwei LanLiyi ShiDanhong ChengLupeng HanDengsong Zhang . NOx reduction against alkali poisoning over Ce(SO4)2-V2O5/TiO2 catalysts by constructing the Ce4+–SO42− pair sites. Chinese Chemical Letters, 2024, 35(5): 108240-. doi: 10.1016/j.cclet.2023.108240

    17. [17]

      Jianyu Qin Yuejiao An Yanfeng ZhangIn Situ Assembled ZnWO4/g-C3N4 S-Scheme Heterojunction with Nitrogen Defect for CO2 Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002

    18. [18]

      Zhi Zhu Xiaohan Xing Qi Qi Wenjing Shen Hongyue Wu Dongyi Li Binrong Li Jialin Liang Xu Tang Jun Zhao Hongping Li Pengwei Huo . Fabrication of graphene modified CeO2/g-C3N4 heterostructures for photocatalytic degradation of organic pollutants. Chinese Journal of Structural Chemistry, 2023, 42(12): 100194-100194. doi: 10.1016/j.cjsc.2023.100194

    19. [19]

      Shuo LiXinran LiuYongjie ZhengJun MaShijie YouHeshan Zheng . Effective peroxydisulfate activation by CQDs-MnFe2O4@ZIF-8 catalyst for complementary degradation of bisphenol A by free radicals and non-radical pathways. Chinese Chemical Letters, 2024, 35(5): 108971-. doi: 10.1016/j.cclet.2023.108971

    20. [20]

      Wei Zhong Dan Zheng Yuanxin Ou Aiyun Meng Yaorong Su . K原子掺杂高度面间结晶的g-C3N4光催化剂及其高效H2O2光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005

Metrics
  • PDF Downloads(0)
  • Abstract views(602)
  • HTML views(0)

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