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
来源：
CATALYSIS COMMUNICATIONS | 2019年 / 119卷
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
相关论文
共 35 条
[1]   Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles [J].
Anbarasan, Pazhamalai ;
Schareina, Thomas ;
Beller, Matthias .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5049-5067
[2]   Aerobic oxidation of alcohols to carbonyl compounds mediated by poly(ethylene glycol)-supported TEMPO radicals [J].
Benaglia, M ;
Puglisi, A ;
Holczknecht, O ;
Quici, S ;
Pozzi, G .
TETRAHEDRON, 2005, 61 (51) :12058-12064
[3]  
Benaglia M., 2009, RECOVERABLE RECYCLAB
[4]   Using soluble polymers to recover catalysts and ligands [J].
Bergbreiter, DE .
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 [J].
Chinnusamy, Tamilselvi ;
Rodionov, Valentin ;
Kuehn, Fritz E. ;
Reiser, Oliver .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (09) :1827-1831
[6]   Immobilization of organic catalysts: When, why, and how [J].
Cozzi, Franco .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) :1367-1390
[7]   Soluble polymers as scaffolds for recoverable catalysts and reagents [J].
Dickerson, TJ ;
Reed, NN ;
Janda, KD .
CHEMICAL REVIEWS, 2002, 102 (10) :3325-3343
[8]   Iron Nitrate/TEMPO: a Superior Homogeneous Catalyst for Oxidation of Primary Alcohols to Nitriles in Air [J].
Dighe, Shashikant U. ;
Chowdhury, Deepan ;
Batra, Sanjay .
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 [J].
Ding, Shengtao ;
Jiao, Ning .
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 [J].
Dornan, Laura M. ;
Cao, Qun ;
Flanagan, James C. A. ;
Crawford, James J. ;
Cook, Matthew J. ;
Muldoon, Mark J. .
CHEMICAL COMMUNICATIONS, 2013, 49 (54) :6030-6032
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