Preparation of tertiary amines via the oxidative coupling of polyfunctional aryl and heteroaryl amidocuprates

被引:29
作者
Kienle, Marcel [1 ]
Dubbaka, Srinivas Reddy [1 ]
del Amo, Vicente [1 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
来源
SYNTHESIS-STUTTGART | 2007年 / 08期
关键词
amination; amidocuprates; C-N bond formation; lithium amides; polyfunctional Grignard reagents;
D O I
10.1055/s-2007-965941
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly functionalized tertiary amines can be prepared by the oxidative coupling of polyfunctional lithium amidocuprates using chloranil as an oxidant. A high functional group tolerance and insensibility to steric hindrance characterize this general amination reaction. Herein, we report a practical procedure for the preparation of aryl and heteroaryl tertiary amines.
引用
收藏
页码:1272 / 1278
页数:7
相关论文
共 38 条
[1]   Oxidative intramolecular coupling of amidocuprates as a novel route to amines and hydrazines [J].
Alberti, A ;
Cane, F ;
Dembech, P ;
Lazzari, D ;
Ricci, A ;
Seconi, G .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1677-1681
[2]   A general and convenient procedure for the synthesis of N-alkylarylamines and N-alkylheteroarylamines by electrophilic amination of cuprates with N-alkylhydroxylamines [J].
Bernardi, P ;
Dembech, P ;
Fabbri, G ;
Ricci, A ;
Seconi, G .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) :641-643
[3]   Industrial R&D on catalytic C-C and C-N coupling reactions: A personal account on goals, approaches and results [J].
Blaser, HU ;
Indolese, A ;
Naud, F ;
Nettekoven, U ;
Schnyder, A .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1583-1598
[4]  
Braig T, 2000, MACROMOL RAPID COMM, V21, P583
[5]  
Cane F, 1997, SYNTHESIS-STUTTGART, P545
[6]   ELECTROPHILIC AMINATION OF HIGHER-ORDER CUPRATES WITH N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE [J].
CASARINI, A ;
DEMBECH, P ;
LAZZARI, D ;
MARINI, E ;
REGINATO, G ;
RICCI, A ;
SECONI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5620-5623
[7]  
Czarnik AW, 1996, ACCOUNTS CHEM RES, V29, P112, DOI 10.1021/ar950256n
[8]   General preparation of primary, secondary, and tertiary aryl amines by the oxidative coupling of polyfunctional aryl and heteroaryl amidocuprates [J].
del Amo, Vicente ;
Dubbaka, Srinivas Reddy ;
Krasovskiy, Arkady ;
Knochel, Paul .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7838-7842
[9]   Conducting polymers prepared by oxidative polymerization: Polyaniline [J].
Gospodinova, N ;
Terlemezyan, L .
PROGRESS IN POLYMER SCIENCE, 1998, 23 (08) :1443-1484
[10]   New indicators for oxidimetry - Some phenanthroline and diphenylamine derivatives [J].
Hammett, LP ;
Walden, GH ;
Edmonds, SM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 :1092-1094