Copper-Mediated 1,4-Diamination of 1,3-Butadienes

被引：15
作者：
Martinez, Claudio [1 ]
Martinez, Luis [1 ]
Kirsch, Jonathan [1 ]
Escudero-Adan, Eduardo C. [1 ]
Martin, Eddy [1 ]
Muniz, Kilian [1 ,2 ]
机构：
[1] ICIQ Inst Chem Res Catalonia, Tarragona 43007, Spain
[2] ICREA Catalan Inst Res & Adv Studies, Barcelona 08010, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 10期
关键词：
Amination; Copper; Dienes; Oxidation; Regioselectivity; CU(I)-CATALYZED REGIOSELECTIVE DIAMINATION; PROMOTED INTRAMOLECULAR DIAMINATION; PALLADIUM-CATALYZED DIAMINATION; OSMIUM IMIDO COMPLEXES; METAL-FREE DIAMINATION; ASYMMETRIC DIAMINATION; CONJUGATED DIENES; OXIDATIVE DIAMINATION; TERMINAL OLEFINS; PD(0)-CATALYZED DIAMINATION;
D O I：
10.1002/ejoc.201301805
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper(II)-mediated diamination of 1,3-butadienes is reported. The reaction employs an inorganic base, copper dibromide as a reagent, and saccharin as the nitrogen source. The diamination proceeds for a series of 1,3-butadienes under relatively mild conditions with complete selectivity in favor of the 1,4-oxidation products.
引用
收藏
页码：2017 / 2021
页数：5
相关论文
共 87 条
[31]  
Farid U., 2012, ANGEW CHEM, V124, P3518, DOI DOI 10.1002/ANGE.201107703
[32]   Highly Stereoselective Metal-Free Oxyaminations Using Chiral Hypervalent Iodine Reagents [J].
Farid, Umar ;
Wirth, Thomas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (14) :3462-3465
[33]  
Frydman B. J., 1998, PCT Int. Appl., Patent No. [WO 9817624 A1 19980430, 9817624]
[34]  
Frydman B. J., 1999, U.S. Patent, Patent No. [US 5889061 A 19990330, 5889061, 5,889,061]
[35]   FUNGICIDAL ACTIVITY OF THE SYNTHETIC PUTRESCINE ANALOG, (E)-1,4-DIAMINOBUT-2-ENE, AND DERIVATIVES [J].
HAVIS, ND ;
WALTERS, DR ;
FOSTER, SA ;
MARTIN, WP ;
COOK, FM ;
ROBINS, DJ .
PESTICIDE SCIENCE, 1994, 41 (01) :61-69
[36]  
Hester J. B., 1992, PCT Int. Appl., Patent No. [WO 9217490 A1 19921015, 9217490]
[37]   High-valent organometallic copper and palladium in catalysis [J].
Hickman, Amanda J. ;
Sanford, Melanie S. .
NATURE, 2012, 484 (7393) :177-185
[38]   Direct synthesis of bicyclic guanidines through unprecedented palladium(II) catalysed diamination with copper chloride as oxidant [J].
Hovelmann, Claas H. ;
Streuff, Jan ;
Brelot, Lydia ;
Muniz, Kilian .
CHEMICAL COMMUNICATIONS, 2008, (20) :2334-2336
[39]  
Iglesias A., 2010, ANGEW CHEM, V122, P8286
[40]   An Intermolecular Palladium-Catalyzed Diamination of Unactivated Alkenes [J].
Iglesias, Alvaro ;
Perez, Edwin G. ;
Muniz, Kilian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) :8109-8111
123456789