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

[1] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES
BRINGMANN, G
WALTER, R
WEIRICH, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09): : 977 - 991
[2] Pd-catalyzed cross-coupling of alkynylsilanols with iodobenzenes
Chang, S
Yang, SH
Lee, PH
[J]. TETRAHEDRON LETTERS, 2001, 42 (29) : 4833 - 4835
[3] Cross-coupling reactions of organosilicon compounds: New concepts and recent advances
Denmark, SE
Sweis, RF
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (12) : 1531 - 1541
[4] Fluoride-free cross-coupling of organosilanols
Denmark, SE
Sweis, RF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (26) : 6439 - 6440
[5] Synthesis of unsymmetrical biaryls from arylsilacyclobutanes
Denmark, SE
Wu, ZC
[J]. ORGANIC LETTERS, 1999, 1 (09) : 1495 - 1498
[6] Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[7] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS
FARINA, V
KRISHNAN, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) : 9585 - 9595
[8] A new method for the synthesis of ketones: The palladium-catalyzed cross-coupling of acid chlorides with arylboronic acids
Haddach, M
McCarthy, JR
[J]. TETRAHEDRON LETTERS, 1999, 40 (16) : 3109 - 3112
[9] NaOH-promoted cross-coupling reactions of organosilicon compounds with organic halides: Practical routes to biaryls, alkenylarenes and conjugated dienes
Hagiwara, E
Gouda, K
Hatanaka, Y
Hiyama, T
[J]. TETRAHEDRON LETTERS, 1997, 38 (03) : 439 - 442
[10] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction
Hassan, J
Sévignon, M
Gozzi, C
Schulz, E
Lemaire, M
[J]. CHEMICAL REVIEWS, 2002, 102 (05) : 1359 - 1469

← 1 2 3 4 →