An improved synthesis of bis(1,3-di-N-tert-butylimidazol-2-ylidene)palladium(0) and its use in C-C and C-N coupling reactions

被引:86
作者
Caddick, S [1 ]
Cloke, FGN
Clentsmith, GKB
Hitchcock, PB
McKerrecher, D
Titcomb, LR
Williams, MRV
机构
[1] Univ Sussex, CPES, Chem Lab, Brighton BN1 9QJ, E Sussex, England
[2] AstraZeneca, Macclesfield SK10 4TF, Cheshire, England
基金
英国工程与自然科学研究理事会;
关键词
N-heterocyclic carbenes; aminations; coupling reactions; palladium complexes;
D O I
10.1016/S0022-328X(00)00724-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new, improved synthesis of [Pd{CN(Bu-t)(CH)(2)N(Bu-t)}(2)] (1) and its use as a catalyst in coupling reactions, including aminations, is presented. An interesting side product formed in the synthesis of 1, [Pd(eta (3)-C4H7) (CN(Bu-t)(CH)(2)N(Bu-t)}Cl] (2), is also discussed. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:635 / 639
页数:5
相关论文
共 31 条
[1]  
ALCAZARROMAN LM, 1999, J ORG CHEM, V64, P5575
[2]  
[Anonymous], 1998, TRANSITION METALS OR
[3]   Metal vapor synthesis as a straightforward route to group 10 homoleptic carbene complexes [J].
Arnold, PL ;
Cloke, FGN ;
Geldbach, T ;
Hitchcock, PB .
ORGANOMETALLICS, 1999, 18 (16) :3228-3233
[4]   N-heterocyclic carbenes Part 26.: N-heterocyclic carbene complexes of palladium(0):: synthesis and application in the Suzuki cross-coupling reaction [J].
Böhm, VPW ;
Gstöttmayr, CWK ;
Weskamp, T ;
Herrmann, WA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 595 (02) :186-190
[5]   Studies toward the synthesis of natural and unnatural dienediynes 1. Approaches to a functionalised bicyclic ring system [J].
Caddick, S ;
Delisser, VM ;
Doyle, VE ;
Khan, S ;
Avent, AG ;
Vile, S .
TETRAHEDRON, 1999, 55 (09) :2737-2754
[6]   TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) [J].
COULSON, DR .
INORGANIC SYNTHESES, 1990, 28 :107-109
[7]   PARAMAGNETIC PHOSPHINE SHIFT-REAGENTS .2. STUDY OF THE STRUCTURES OF (SUBSTITUTED-ALLYL)PALLADIUM COMPLEXES IN SOLUTION [J].
FALLER, JW ;
BLANKENSHIP, C ;
WHITMORE, B ;
SENA, S .
INORGANIC CHEMISTRY, 1985, 24 (26) :4483-4490
[8]  
Green JC, 1997, CHEM COMMUN, P1963
[9]   Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates [J].
Hamann, BC ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) :7369-7370
[10]   Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand [J].
Hartwig, JF ;
Kawatsura, M ;
Hauck, SI ;
Shaughnessy, KH ;
Alcazar-Roman, LM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5575-5580