Electrochemical synthesis of nitriles from aldehydes using TEMPO as a mediator

被引：39

作者：

Chen, Qiguo ^{[1
]}

Fang, Chaojie ^{[1
]}

Shen, Zhenlu ^{[1
]}

Li, Meichao ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China

来源：

ELECTROCHEMISTRY COMMUNICATIONS | 2016年 / 64卷

关键词：

Electrosynthsis; Nitriles; TEMPO; Aldehydes; Hexamethyldisilazane; PALLADIUM-CATALYZED CYANATION; OXIDATIVE CONVERSION; PRIMARY AMIDES; ARYL HALIDES; ALCOHOLS; SYSTEM; TRANSFORMATION; DERIVATIVES; AMMONIA; AMINES;

D O I：

10.1016/j.elecom.2016.01.011

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

A novel electrochemical route to generate nitriles from aldehydes under mild conditions using a catalytic amount of TEMPO (2,2,6,6-tetramethylpiperidinyl-1-oxy) as the mediator and hexamethyldisilazane as the nitrogen source in the presence of acetic acid has been developed. A variety of aromatic, heteroaromatic and aliphatic aldehydes have been converted to their corresponding nitriles in good to excellent yields. A plausible reaction mechanism is proposed based on the cyclic voltammetry, in situ FTIR and the identification of intermediates. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：51 / 55

页数：5

共 40 条

[1] Synthetic applications of nonmetal catalysts for homogeneous oxidations [J].

Adam, W ;

Saha-Möller, CR ;

Ganeshpure, PA .

CHEMICAL REVIEWS, 2001, 101 (11) :3499-3548

[2] 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

[3] Catalytic Sandmeyer cyanation as a synthetic pathway to aryl nitriles [J].

Beletskaya, IP ;

Sigeev, AS ;

Peregudov, AS ;

Petrovskii, PV .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (23) :3810-3812

[4] 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

[5] The importance of Green Chemistry in Process Research and Development [J].

Dunn, Peter J. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) :1452-1461

[6] Copper-Catalyzed Decarboxylative CN Triple Bond Formation: Direct Synthesis of Benzonitriles from Phenylacetic Acids Under O2 Atmosphere [J].

Feng, Qiang ;

Song, Qiuling .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (08) :1697-1702

[7] Redox catalysis in organic electrosynthesis: basic principles and recent developments [J].

Francke, Robert ;

Little, R. Daniel .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2492-2521

[8]

Furlan, 2008, REV BRAS APL VACUO, V25, P45

[9] Novel trans-spanned palladium complexes as efficient catalysts in mild and amine-free cyanation of aryl bromides under air [J].

Grossman, O ;

Gelman, D .

ORGANIC LETTERS, 2006, 8 (06) :1189-1191

[10] Diethylaminotrimethylsilane mediated aldol condensation of naked aldehydes [J].

Hagiwara, H ;

Ono, H ;

Komatsubara, N ;

Hoshi, T ;

Suzuki, T ;

Ando, M .

TETRAHEDRON LETTERS, 1999, 40 (36) :6627-6630

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