Recyclable MeOPEG-clicked TEMPO catalyst for one-pot aerobic double dehydrogenation of alcohols to nitriles

被引:9
作者
Chinnusamy, Tamilselvi [1 ]
机构
[1] Indian Inst Sci Educ & Res, Sch Chem, Vithura Campus, Thiruvananthapuram 695551, Kerala, India
关键词
MeOPEG-clicked TEMPO; Nitriles; Recyclable catalyst; Dehydrogenation of alcohols; Click reaction; POLY(ETHYLENE GLYCOL)-SUPPORTED TEMPO; OXIDATIVE SYNTHESIS; SELECTIVE OXIDATION; BENZYLIC ALCOHOLS; SOLUBLE POLYMERS; PRIMARY AMINES; ARYL NITRILES; CYANATION; N; N-DIMETHYLFORMAMIDE; IMMOBILIZATION;
D O I
10.1016/j.catcom.2018.08.021
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In this study, TEMPO was efficiently grafted on MeOPEG support by copper-catalyzed (3 + 2) cycloaddition reaction. The newly immobilized MeOPEG-clicked TEMPO catalyst was characterized by NMR, IR, and MALDI-TOF. Subsequently, it was used for one-pot aerobic double dehydrogenation of alcohols to nitriles using aqueous ammonia as the nitrogen source and O-2 (1 atm) as the terminal oxidant. The catalytic efficiency was also reported with various benzyl, alkyl, and heteroaromatic alcohols. The reactivity of this catalyst is comparable with that of unmodified TEMPO. Furthermore, the new MeOPEG-clicked TEMPO catalyst could be easily recovered by precipitation and recycled up to five runs.
引用
收藏
页码:51 / 56
页数:6
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共 35 条
  • [1] Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles
    Anbarasan, Pazhamalai
    Schareina, Thomas
    Beller, Matthias
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5049 - 5067
  • [2] Aerobic oxidation of alcohols to carbonyl compounds mediated by poly(ethylene glycol)-supported TEMPO radicals
    Benaglia, M
    Puglisi, A
    Holczknecht, O
    Quici, S
    Pozzi, G
    [J]. TETRAHEDRON, 2005, 61 (51) : 12058 - 12064
  • [3] Benaglia M., 2009, RECOVERABLE RECYCLAB
  • [4] Using soluble polymers to recover catalysts and ligands
    Bergbreiter, DE
    [J]. CHEMICAL REVIEWS, 2002, 102 (10) : 3345 - 3383
  • [5] Update: An Efficient Synthesis of Poly(ethylene glycol)-Supported Iron(II) Porphyrin Using a Click Reaction and its Application for the Catalytic Olefination of Aldehydes
    Chinnusamy, Tamilselvi
    Rodionov, Valentin
    Kuehn, Fritz E.
    Reiser, Oliver
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (09) : 1827 - 1831
  • [6] Immobilization of organic catalysts: When, why, and how
    Cozzi, Franco
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) : 1367 - 1390
  • [7] Soluble polymers as scaffolds for recoverable catalysts and reagents
    Dickerson, TJ
    Reed, NN
    Janda, KD
    [J]. CHEMICAL REVIEWS, 2002, 102 (10) : 3325 - 3343
  • [8] Iron Nitrate/TEMPO: a Superior Homogeneous Catalyst for Oxidation of Primary Alcohols to Nitriles in Air
    Dighe, Shashikant U.
    Chowdhury, Deepan
    Batra, Sanjay
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (18) : 3892 - 3896
  • [9] Direct Transformation of N,N-Dimethylformamide to -CN: Pd-Catalyzed Cyanation of Heteroarenes via C-H Functionalization
    Ding, Shengtao
    Jiao, Ning
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) : 12374 - 12377
  • [10] Copper/TEMPO catalysed synthesis of nitriles from aldehydes or alcohols using aqueous ammonia and with air as the oxidant
    Dornan, Laura M.
    Cao, Qun
    Flanagan, James C. A.
    Crawford, James J.
    Cook, Matthew J.
    Muldoon, Mark J.
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (54) : 6030 - 6032