Copper-catalyzed C-N bond formation using dialkyl azodicarboxylate as the amination reagent

被引:9
作者
Samzadeh-Kermani, Alireza [1 ]
机构
[1] Univ Zabol, Dept Chem, Fac Sci, Zabol, Iran
关键词
Aryl hydrazide; C-N cross-coupling; Copper salts; Dialkyl azodicarboxylate; ARYL; ALKYLATION;
D O I
10.1016/j.tetlet.2015.12.036
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient copper-catalyzed reaction for C-N bond formation using aryl halides, dialkyl azodicarboxylate, and a hydride source is reported. Using this procedure, aryl iodides reacted at ambient conditions, while aryl bromides required heating to 60 degrees C to accomplish the transformation. Various functional groups were tolerated under the optimum conditions. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:463 / 465
页数:3
相关论文
共 16 条
[1]   Use of polyanions for alkylation of hydrazine derivatives [J].
Bredihhin, Aleksei ;
Maeorg, Uno .
ORGANIC LETTERS, 2007, 9 (24) :4975-4977
[2]   ADDITION OF ARYLMETALLICS TO AZODICARBOXYLATES - A NOVEL SYNTHESIS OF ARYLHYDRAZINES BY AROMATIC HYDRAZINATION [J].
DEMERS, JP ;
KLAUBERT, DH .
TETRAHEDRON LETTERS, 1987, 28 (42) :4933-4934
[3]   Formation of aryl-nitrogen bonds using a soluble copper(I) catalyst [J].
Gujadhur, R ;
Venkataraman, D ;
Kintigh, JT .
TETRAHEDRON LETTERS, 2001, 42 (29) :4791-4793
[4]   An efficient copper-catalyzed coupling of aryl halides with imidazoles [J].
Kiyomori, A ;
Marcoux, JF ;
Buchwald, SL .
TETRAHEDRON LETTERS, 1999, 40 (14) :2657-2660
[5]   Kinetic Investigation of a Ligand-Accelerated Sub-mol% Copper-Catalyzed C-N Cross-Coupling Reaction [J].
Larsson, Per-Fredrik ;
Bolm, Carsten ;
Norrby, Per-Ola .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (46) :13613-13616
[6]   An Improved and Mild Wenker Synthesis of Aziridines [J].
Li, Xinyao ;
Chen, Ning ;
Xu, Jiaxi .
SYNTHESIS-STUTTGART, 2010, (20) :3423-3428
[7]   Palladium-catalyzed formation of diaryl ethers from aryl bromides. Electron poor phosphines enhance reaction yields [J].
Mann, G ;
Hartwig, JF .
TETRAHEDRON LETTERS, 1997, 38 (46) :8005-8008
[8]   N-Cumyl benzamide, sulfonamide, and aryl O-carbamate directed metalation groups.: Mild hydrolytic lability for facile manipulation of directed ortho metalation derived aromatics [J].
Metallinos, C ;
Nerdinger, S ;
Snieckus, V .
ORGANIC LETTERS, 1999, 1 (08) :1183-1186
[9]   Chemoselective reductive alkylation of ammonia with carbonyl compounds: synthesis of primary and symmetrical secondary amines [J].
Miriyala, B ;
Bhattacharyya, S ;
Williamson, JS .
TETRAHEDRON, 2004, 60 (07) :1463-1471
[10]   Antimalarial compounds: from bench to bedside [J].
Olliaro, PL ;
Taylor, WRJ .
JOURNAL OF EXPERIMENTAL BIOLOGY, 2003, 206 (21) :3753-3759