N-Heterocyclic Carbenes (NHCs) Containing N-C-Palladacycle Complexes: Synthesis and Reactivity in Aryl Amination Reactions

被引:81
作者
Broggi, Julie [1 ]
Clavier, Herve [1 ]
Nolan, Steven P. [1 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
关键词
D O I
10.1021/om8006689
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Starting from the corresponding dimer, new saturated NHC-containing N,N-dimethyl biphenylamine (DMBPA) palladacycle complexes have been synthesized and fully characterized. Catalytic activity of these well-defined, air- and moisture-stable palladium(II) complexes was evaluated in the Buchwald-Hartwig amination involving a range of unactivated aryl chlorides. From a practical perspective, the reaction conditions required when using [(NHC)Pd(palladacycle)Cl] systems are very appealing. The organic biphenyl ligand used in the synthesis of the pallaclacycles has been synthesized using a Suzuki-Miyaura cross-coupling employing the novel palladacycle-NHC complexes.
引用
收藏
页码:5525 / 5531
页数:7
相关论文
共 73 条
[1]   Pyrrole-2-carboxylic acid as a ligand for the Cu-catalyzed reactions of primary anilines with aryl halides [J].
Altman, Ryan A. ;
Anderson, Kevin W. ;
Buchwald, Stephen L. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) :5167-5169
[2]   Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].
Antilla, JC ;
Baskin, JM ;
Barder, TE ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587
[3]   Reactivity of arylic carbanions generated by reductive cleavage of C-N bond of N,N-dimethylanilines [J].
Azzena, U ;
Cattari, M ;
Melloni, G ;
Pisano, L .
SYNTHESIS-STUTTGART, 2003, (18) :2811-2814
[4]   Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions [J].
Bedford, RB .
CHEMICAL COMMUNICATIONS, 2003, (15) :1787-1796
[5]   Palladacycles in catalysis - a critical survey [J].
Beletskaya, IP ;
Cheprakov, AV .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :4055-4082
[6]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[7]  
Boeda F, 2008, ANNU REP PROG CHEM B, V104, P184, DOI 10.1039/b716604b
[8]   A novel series of p38 MAP kinase inhibitors for the potential treatment of rheumatoid arthritis [J].
Brown, DS ;
Belfield, AJ ;
Brown, GR ;
Campbell, D ;
Foubister, A ;
Masters, DJ ;
Pike, KG ;
Snelson, WL ;
Wells, SL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (21) :5383-5387
[9]   PHOTOINDUCED ELECTRON-TRANSFER REACTION OF ARYL PERFLUOROALKANESULFONATES WITH ANILINES [J].
CHEN, QY ;
LI, ZT .
JOURNAL OF FLUORINE CHEMISTRY, 1994, 66 (01) :59-62
[10]  
Clavier H, 2007, ANNU REP PROG CHEM B, V103, P193, DOI 10.1039/b614412h