A highly active Suzuki catalyst for the synthesis of sterically hindered biaryls: Novel ligand coordination

被引:501
作者
Yin, JJ [1 ]
Rainka, MP [1 ]
Zhang, XX [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja017082r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A catalyst system for the preparation of biaryls containing four ortho substituents via Suzuki coupling is described. The combination of a catalytic quantity of Pd2(dba)3 with either an electron-rich biarylphosphine or DPEPhos is effective using a wide range of substrates. The X-ray crystal structure of (dba)Pd(2-(9-phenanthryl)phenyl-dicyclohexylphosphine), in which the Pd is coordinated to the 9,10-double bond of the phenanthryl group, is also reported. Copyright © 2002 American Chemical Society.
引用
收藏
页码:1162 / 1163
页数:2
相关论文
共 33 条
[1]   A modified in situ Suzuki cross-coupling of haloarenes for the preparation of C-2-symmetric biaryls [J].
Andersen, NG ;
Maddaford, SP ;
Keay, BA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9556-9559
[2]   Investigations into ambient temperature biaryl coupling reactions [J].
Anderson, JC ;
Namli, H ;
Roberts, CA .
TETRAHEDRON, 1997, 53 (44) :15123-15134
[3]   Palladacyclic phosphinite complexes as extremely high activity catalysts in the Suzuki reaction [J].
Bedford, RB ;
Welch, SL .
CHEMICAL COMMUNICATIONS, 2001, (01) :129-130
[4]   Palladium/P,O-ligand-catalyzed Suzuki cross-coupling reactions of arylboronic acids and aryl chlorides. Isolation and structural characterization of (P,O)-Pd(dba) complex [J].
Bei, XH ;
Turner, HW ;
Weinberg, WH ;
Guram, AS ;
Petersen, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6797-6803
[5]   The first asymmetric Suzuki cross-coupling reaction [J].
Cammidge, AN ;
Crépy, KVL .
CHEMICAL COMMUNICATIONS, 2000, (18) :1723-1724
[6]  
CARROLL FA, 1998, PERSPECTIVES STRUCTU, P213
[7]   Suzuki cross-coupling reaction of sterically hindered aryl boronates with 3-iodo-4-methoxybenzoic acid methylester [J].
Chaumeil, H ;
Signorella, S ;
Le Drian, C .
TETRAHEDRON, 2000, 56 (49) :9655-9662
[8]   The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst [J].
Dai, CY ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2719-2724
[9]   CATALYTIC ASYMMETRIC REDUCTION OF ALLYLIC ESTERS WITH FORMIC-ACID CATALYZED BY PALLADIUM MOP COMPLEXES [J].
HAYASHI, T ;
IWAMURA, H ;
NAITO, M ;
MATSUMOTO, Y ;
UOZUMI, Y ;
MIKI, M ;
YANAGI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :775-776
[10]   Chiral monodentate phosphine ligand MOP for transition metal-catalyzed asymmetric reactions [J].
Hayashi, T .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :354-362