One-pot aromatic amination based on carbon-nitrogen coupling reaction between aryl halides and azido compounds

被引：46

作者：

Maejima, Toshihide ^{[1
]}

Shimoda, Yutaka ^{[1
]}

Nozaki, Kei ^{[1
]}

Mori, Shigeki ^{[1
]}

Sawama, Yoshinari ^{[1
]}

Monguchi, Yasunari ^{[1
]}

Sajiki, Hironao ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Organ Chem Lab, Gifu 5011196, Japan

来源：

TETRAHEDRON | 2012年 / 68卷 / 06期

关键词：

Amination; Reduction; Azides; Copper; Cross-coupling; CATALYZED LIGAND-FREE; HETEROGENEOUS PD/C; SODIUM-AZIDE; C-N; COPPER; PALLADIUM; AMMONIA; ANILINES; ULLMANN; AMINES;

D O I：

10.1016/j.tet.2011.12.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient copper-mediated C-N coupling reaction between various aryl halides and azido compounds to produce the corresponding aromatic primary amines was established. The present amination is apparently involved in both the reduction of an azido functionality to the corresponding primary amino group and its cross-coupling reaction with aryl halides in a one-pot manner. The present amination could be applied to the synthesis of procaine, a local anesthetic drug. A mechanistic study indicated that 2-aminoethanol could work as a major hydrogen donor and the reaction would proceed without the formation of the intermediary aryl azide. (C) 2011 Elsevier Ltd. All rights reserved,

引用

页码：1712 / 1722

页数：11

共 29 条

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