Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates

被引：62

作者：

Denmark, SE ^{[1
]}

Sweis, RF ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 21期

关键词：

D O I：

10.1021/ol026900x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] The design and development of an effective protocol for the palladium-catalyzed cross-coupling of (E)- and (Z)-heptenyidimethylsilanois with organo-triflates and nonaflates is described. Optimization of this coupling focused on the issues of both reactivity and stability of the psuedohalides in the presence of the nucleophilic fluoride promoter for the coupling. The crucial role of varying amounts of water to modulate the reactivity of the fluoride ion is highlighted.

引用

页码：3771 / 3774

页数：4

共 35 条

[1] Palladium-imidazolium carbene catalyzed aryl, vinyl, and alkyl Suzuki-Miyaura cross coupling
Andrus, MB
Song, C
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3761 - 3764
[2] [Anonymous], METAL CATALYZED CROS
[3] A novel regio- and stereoselective formal cross-coupling reaction of unsaturated silanes with arenediazonium tetrafluoroborates
Babudri, F
Farinola, GM
Naso, F
Panessa, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) : 1554 - 1557
[4] SYNTHESES, PROPERTIES, AND STRUCTURES OF ANHYDROUS TETRAMETHYLAMMONIUM FLUORIDE AND ITS 1-1 ADDUCT WITH TRANS-3-AMINO-2-BUTENENITRILE
CHRISTE, KO
WILSON, WW
WILSON, RD
BAU, R
FENG, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) : 7619 - 7625
[5] On the nature of fluoride ion hydration
Craig, JDC
Brooker, MH
[J]. JOURNAL OF SOLUTION CHEMISTRY, 2000, 29 (10) : 879 - 888
[6] Design and implementation of new, silicon-based, cross-coupling reactions: Importance of silicon-oxygen bonds
Denmark, SE
Sweis, RF
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) : 835 - 846
[7] Highly stereospecific, palladium-catalyzed cross-coupling of alkenylsilanols
Denmark, SE
Wehrli, D
[J]. ORGANIC LETTERS, 2000, 2 (04) : 565 - 568
[8] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES
ECHAVARREN, AM
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5478 - 5486
[9] FARINA V, 1998, J ORG REACT, V50, P1
[10] A WIDE-RANGE OF ORGANOSILICON COMPOUNDS COUPLES WITH ENOL AND ARYL TRIFLATES IN THE PRESENCE OF PD CATALYST AND FLUORIDE-ION
HATANAKA, Y
HIYAMA, T
[J]. TETRAHEDRON LETTERS, 1990, 31 (19) : 2719 - 2722

← 1 2 3 4 →