Cross-coupling reactions of arylsilanols with substituted aryl halides

被引：98

作者：

Denmark, SE ^{[1
]}

Ober, MH ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 08期

关键词：

D O I：

10.1021/ol034328j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed cross-coupling of arylsilanols with aryl iodides and aryl bromides (in the presence of cesium carbonate) furnished various biaryl products in high yield. An extensive series of optimizations led to the identification of key variables, including activator, solvent, catalyst, and hydration level, that influence the rate and selectivity of the process. Manipulation of these features provided an effective coupling method of wide scope and generality.

引用

页码：1357 / 1360

页数：4

共 39 条

[11] HIGHLY SELECTIVE CROSS-COUPLING REACTIONS OF ARYL(HALO)SILANES WITH ARYL HALIDES - A GENERAL AND PRACTICAL ROUTE TO FUNCTIONALIZED BIARYLS
HATANAKA, Y
GODA, K
OKAHARA, Y
HIYAMA, T
[J]. TETRAHEDRON, 1994, 50 (28) : 8301 - 8316
[12] 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
[13] Heck R.F., 1985, PALLADIUM REAGENTS O
[14] Palladium-catalyzed (Ullmann-Type) homocoupling of aryl halides: A convenient and general synthesis of symmetrical biaryls via inter- and intramolecular coupling reactions
Hennings, DD
Iwama, T
Rawal, VH
[J]. ORGANIC LETTERS, 1999, 1 (08) : 1205 - 1208
[15] Palladium-catalyzed cross-coupling of silanols, silanediols, and silanetriols promoted by silver(I) oxide
Hirabayashi, E
Mori, A
Kawashima, J
Suguro, M
Nishihara, Y
Hiyama, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) : 5342 - 5349
[16] A new transformation of silanols. Palladium-catalyzed cross-coupling with organic halides in the presence of silver(I) oxide
Hirabayashi, K
Kawashima, J
Nishihara, Y
Mori, A
Hiyama, T
[J]. ORGANIC LETTERS, 1999, 1 (02) : 299 - 301
[17] Hiyama T, 2002, TOP CURR CHEM, V219, P61
[18] PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ORGANOMETALLOIDS THROUGH ACTIVATION WITH FLUORIDE-ION
HIYAMA, T
HATANAKA, Y
[J]. PURE AND APPLIED CHEMISTRY, 1994, 66 (07) : 1471 - 1478
[19] Hiyama T, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P421
[20] Solid phase cross-coupling reaction of aryl(halo)silanes with 4-iodobenzoic acid
Homsi, F
Hosoi, K
Nozaki, K
Hiyama, T
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 208 - 216

← 1 2 3 4 →