Synthesis of a C3-symmetric ferrocenylphosphine and its application to the Suzuki reaction of aryl chlorides

被引:42
作者
Pickett, TE [1 ]
Richards, CJ [1 ]
机构
[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales
关键词
D O I
10.1016/S0040-4039(01)00568-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(S-p,S-p,S-p)-Tris(2-methyl ferrocenyl)phosphine 1 was synthesised in 62% yield from (S)-2-ferrocenyl-4-(1-methylethyl)oxazoline. In combination with Pd(2)dba(3) this novel C-3-symmetric ligand generates a catalyst for the Suzuki reaction of aryl chloride substrates, these reactions proceed readily at 60 degreesC in dioxane. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3767 / 3769
页数:3
相关论文
共 21 条
[1]  
ALLENMAR.S, 1974, TETRAHEDRON LETT, P371
[2]   The first asymmetric Suzuki cross-coupling reaction [J].
Cammidge, AN ;
Crépy, KVL .
CHEMICAL COMMUNICATIONS, 2000, (18) :1723-1724
[3]   Highly active and selective catalysts for the formation of α-aryl ketones [J].
Fox, JM ;
Huang, XH ;
Chieffi, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370
[4]   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
[5]   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
[6]   Palladacycles: Efficient new catalysts for the Heck vinylation of aryl halides [J].
Herrmann, WA ;
Brossmer, C ;
Reisinger, CP ;
Riermeier, TH ;
Ofele, K ;
Beller, M .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (08) :1357-1364
[7]   Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions [J].
Littke, AF ;
Dai, CY ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4020-4028
[8]  
Littke AF, 1998, ANGEW CHEM INT EDIT, V37, P3387, DOI 10.1002/(SICI)1521-3773(19981231)37:24<3387::AID-ANIE3387>3.0.CO
[9]  
2-P
[10]  
NISHIBAYASHI Y, 1995, SYNLETT, P79