Straightforward Iron-Catalyzed Synthesis of Nitriles by Dehydration of Primary Amides

被引:36
作者
Enthaler, Stephan [1 ]
机构
[1] Tech Univ Berlin, Dept Chem, D-10623 Berlin, Germany
关键词
Iron; Homogeneous catalysis; Dehydration; Amides; Nitriles; MILD; ACID; CARBOXAMIDES; ALDOXIMES; CYANATION; REAGENT;
D O I
10.1002/ejoc.201100754
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the present study, the iron-catalyzed dehydration of a range of amides to the corresponding nitriles by using N-methyl-N-(trimethylsilyl) trifluoroacetamide (MSTFA) as the dehydration reagent has been explored. After investigating different reaction parameters (e. g., iron source, solvent, catalyst loading) with FeCl2 center dot 4H(2)O, an excellent and easily accessible precatalyst was found. The obtained system (5.0 mol-% [Fe], 3.0 equiv. MSTFA) was highly active and dehydrated a broad scope of amides selectively to the corresponding nitriles under mild reaction conditions (THF, 70 degrees C) within two hours (yields: >99%, selectivities: >99%).
引用
收藏
页码:4760 / 4763
页数:4
相关论文
共 61 条
[1]   Origins, current status, and future challenges of green chemistry [J].
Anastas, PT ;
Kirchhoff, MM .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :686-694
[2]  
[Anonymous], ANGEW CHEM
[3]  
[Anonymous], 2009, ANGEW CHEM
[4]   Recent Advances in Iron Catalysis in Organic Synthesis [J].
Bauer, Eike B. .
CURRENT ORGANIC CHEMISTRY, 2008, 12 (16) :1341-1369
[5]   CATALYTIC DECOMPOSITION OF SECONDARY CARBOXAMIDES BY TRANSITION-METAL COMPLEXES [J].
BLUM, J ;
FISHER, A ;
GREENER, E .
TETRAHEDRON, 1973, 29 (08) :1073-1081
[6]  
BLUM J, 1970, TETRAHEDRON LETT, P1963
[7]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[8]   Aryl chlorothionoformate: A new versatile reagent for the preparation of Nitriles and Isonitriles under mild conditions [J].
Bose, DS ;
Goud, PR .
TETRAHEDRON LETTERS, 1999, 40 (04) :747-748
[9]   On the Role of Metal Contaminants in Catalyses with FeCl3 [J].
Buchwald, Stephen L. ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5586-5587
[10]   An iron catalyst for ketone hydrogenations under mild conditions [J].
Bullock, R. Morris .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) :7360-7363