Cyanides-Free Cyanation of Aryl Halides using Formamide

被引：78

作者：

Sawant, Dinesh N. ^{[1
]}

Wagh, Yogesh S. ^{[1
]}

Tambade, Pawan J. ^{[1
]}

Bhatte, Kushal D. ^{[1
]}

Bhanage, Bhalchandra M. ^{[1
]}

机构：

[1] Deemed Univ, Inst Chem Technol, Dept Chem, Bombay 400019, Maharashtra, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 05期

关键词：

aryl halides; C-C coupling; cyanation; formamide; nitriles; palladium; PALLADIUM-CATALYZED CYANATION; MONOXIDE-FREE AMINOCARBONYLATION; POTASSIUM HEXACYANOFERRATE(II); NUCLEOPHILIC DISPLACEMENT; TRANSITION-METAL; BROMIDES; EFFICIENT; SYSTEM; CONVENIENT; COMPLEXES;

D O I：

10.1002/adsc.201000807

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel method for cyanation of aryl halides using formamide as a non-toxic cyanide source is reported. It is a single-step, solvent-free method wherein formamide itself acts as solvent as well as source of cyanide in the presence of phosphorus oxychloride and palladium acetate/xantphos catalyst. Aryl iodides as well as aryl bromides provided moderate to excellent yields of up to 93%.

引用

页码：781 / 787

页数：7

共 50 条

[21] Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media [J].

Cohen, Daniel T. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2015, 17 (02) :202-205

[22] Ligand-free Cul-catalyzed cyanation of aryl halides using K4[Fe(CN)6] as cyanide source and water as solvent [J].

DeBlase, Catherine ;

Leadbeater, Nicholas E. .

TETRAHEDRON, 2010, 66 (05) :1098-1101

[23] Copper-Mediated Cyanation of Aryl Halides by Activation of Benzyl Cyanide as the Cyanide Source [J].

Wen, Qiaodong ;

Jin, Jisong ;

Mei, Yuncai ;

Lu, Ping ;

Wang, Yanguang .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (19) :4032-4036

[24] Highly active recyclable heterogeneous nanonickel ferrite catalyst for cyanation of aryl and heteroaryl halides [J].

Moghaddam, Firouz Matloubi ;

Tavakoli, Ghazal ;

Rezvani, Hamid Reza .

APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (10) :750-755

[25] An efficient palladium catalytic system for microwave assisted cyanation of aryl halides [J].

Hajipour, Abdol R. ;

Karami, Kazem ;

Tavakoli, Ghazal ;

Pirisedigh, Azade .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (04) :819-824

[26] Palladium-catalyzed cyanation of aryl halides: Recent developments and perspectives [J].

Sundermeier, M ;

Zapf, A ;

Beller, M .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2003, (19) :3513-3526

[27] Recent advances and prospects in the palladium-catalyzed cyanation of aryl halides [J].

Neetha, Mohan ;

Afsina, C. M. A. ;

Aneeja, Thaipparambil ;

Anilkumar, Gopinathan .

RSC ADVANCES, 2020, 10 (56) :33683-33699

[28] Heterogeneous Cyanation Reaction of Aryl Halides Catalyzed by a Reusable Palladium Schiff Base Complex in Water [J].

Jiang, Huiliang ;

Jiang, Jianzhong ;

Wei, Huixian ;

Cai, Chun .

CATALYSIS LETTERS, 2013, 143 (11) :1195-1199

[29] Palladium/N-Heterocyclic Carbene Catalyzed Mono- and Double-Cyanation of Aryl Halides Using Potassium Ferrocyanide Trihydrate under Aerobic Conditions [J].

Xu, Zhicheng ;

Xiao, Yunqing ;

Ding, Hong ;

Cao, Changsheng ;

Li, Haitao ;

Pang, Guangsheng ;

Shi, Yanhui .

SYNTHESIS-STUTTGART, 2015, 47 (11) :1560-1566

[30] Palladium nanoparticles-polypyrrole composite as an efficient catalyst for cyanation of aryl halides [J].

Magdesieva, Tatiana V. ;

Nikitin, Oleg M. ;

Zolotukhina, Ekaterina V. ;

Vorotyntsev, Mikhail A. .

ELECTROCHIMICA ACTA, 2014, 122 :289-295

← 1 2 3 4 5 →