An Efficient Oxidation of Primary Azides Catalyzed by Copper Iodide: A Convenient Method for the Synthesis of Nitriles

被引:80
作者
Lamani, Manjunath [1 ]
Prabhu, Kandikere Ramaiah [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
azides; copper; nitriles; oxidation; tert-butyl hydroperoxide; AQUEOUS-MEDIUM; PRIMARY AMIDES; NUCLEOPHILIC-SUBSTITUTION; HETEROGENEOUS CATALYST; MOLYBDENUM XANTHATE; TRANSFORMATION; ALDOXIMES; CYANATION; ALDEHYDES; DEHYDRATION;
D O I
10.1002/anie.201002635
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A wide range of primary azides have been efficiently oxidized by a catalytic amount of CuI and TBHP into their corresponding nitriles in aqueous solution. A variety of oxidizable functional groups were well tolerated under the reaction conditions, and oxidation of secondary azides furnished their corresponding ketones (see scheme; TBHP=tert-butyl hydroperoxide). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6622 / 6625
页数:4
相关论文
共 51 条
[21]  
Kurtz P., 1952, HOUBEN WEYL METHOD 3, V8, P302
[22]  
Larock R.C., 1989, COMPREHENSIVE ORGANI
[23]  
lida S., 2007, TETRAHEDRON, V63, P8274
[24]   COPPER ASSISTED NUCLEOPHILIC-SUBSTITUTION OF ARYL HALOGEN [J].
LINDLEY, J .
TETRAHEDRON, 1984, 40 (09) :1433-1456
[25]   Oxidation and ammoxidation of aromatics [J].
Lücke, B ;
Narayana, KV ;
Martin, A ;
Jähnisch, K .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (12) :1407-1424
[26]   A chemoselective aerobic oxidation of benzylic azides catalyzed by molybdenum xanthate in an aqueous medium [J].
Maddani, Mahagundappa ;
Prabhu, Kandikere Ramaiah .
TETRAHEDRON LETTERS, 2008, 49 (29-30) :4526-4530
[27]   A convenient method for the synthesis of substituted thioureas [J].
Maddani, Mahagundappa ;
Prabhu, Kandikere Ramaiah .
TETRAHEDRON LETTERS, 2007, 48 (40) :7151-7154
[28]   A Concise Synthesis of Substituted Thiourea Derivatives in Aqueous Medium [J].
Maddani, Mahagundappa R. ;
Prabhu, Kandikere R. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (07) :2327-2332
[29]   Chemoselective reduction of azides catalyzed by molybdenum xanthate by using phenylsilane as the hydride source [J].
Maddani, Mahagundappa R. ;
Moorthy, Saravana K. ;
Prabhu, Kandikere R. .
TETRAHEDRON, 2010, 66 (01) :329-333
[30]   Designer magnets containing cyanides and nitriles [J].
Miller, JS ;
Manson, JL .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (07) :563-570