General preparation of primary, secondary, and tertiary aryl amines by the oxidative coupling of polyfunctional aryl and heteroaryl amidocuprates

被引:63
作者
del Amo, Vicente [1 ]
Dubbaka, Srinivas Reddy [1 ]
Krasovskiy, Arkady [1 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
关键词
amination; amines; C-N bond formation; cuprates; Grignard reagents;
D O I
10.1002/anie.200603089
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented). A tolerant reaction: Functionalized tertiary amines have been prepared by the oxidative coupling of amidocuprates with chloranil used as the oxidant (see Scheme). A high tolerance of functional groups and insensitivity to steric hindrance characterize this general amination reaction. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7838 / 7842
页数:5
相关论文
共 64 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]  
[Anonymous], ANGEW CHEM
[3]   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
[4]   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
[5]   Elucidation of optical switching of single guest molecules in terrylene/p-terphenyl mixed crystals [J].
Bordat, P ;
Brown, R .
CHEMICAL PHYSICS LETTERS, 2000, 331 (5-6) :439-445
[6]  
Braig T, 2000, MACROMOL RAPID COMM, V21, P583
[7]  
Cane F, 1997, SYNTHESIS-STUTTGART, P545
[8]   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
[9]   The Heck reaction in the production of fine chemicals [J].
de Vries, JG .
CANADIAN JOURNAL OF CHEMISTRY, 2001, 79 (5-6) :1086-1092
[10]   Facile synthesis and characterization of naphthidines as a new class of highly nonplanar electron donors giving robust radical cations [J].
Desmarets, C ;
Champagne, B ;
Walcarius, A ;
Bellouard, C ;
Omar-Amrani, R ;
Ahajji, A ;
Fort, Y ;
Schneider, R .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1351-1361