Phosphine oxides as stabilizing ligands for the palladium-catalyzed cross-coupling of potassium aryldimethylsilanolates

被引：53

作者：

Denmark, Scott E. ^{[1
]}

Smith, Russell C. ^{[1
]}

Tymonko, Steven A. ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2007年 / 63卷 / 26期

关键词：

cross-coupling; biaryls; phosphine oxides; silanols;

D O I：

10.1016/j.tet.2007.02.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The palladium-catalyzed cross-coupling reaction of potassium (4-methoxyphenyl) dimethylsilanolate (K(+)1(-)) with aryl bromides has been demonstrated using triphenylphosphine oxide as a stabilizing ligand. Unsymmetrical biaryls can be prepared from a variety of aryl bromides in good yield with short reaction times. Qualitative kinetic studies compared effects of different phosphine oxides on the rate of cross-coupling and established the beneficial effect of these ligands in the reaction of electron-rich arylsilanolates. The improved yield and reproducibility of the cross-coupling of several bromides was demonstrated by direct comparison of reactions performed with and without triphenylphosphine oxide under non-rigorous exclusion of oxygen. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：5730 / 5738

页数：9

共 62 条

[1]

[Anonymous], 1999, J CHEM EDUC

[2]

Catalytic asymmetric synthesis of bis-armed aromatic amino acid derivatives. Problems related to the synthesis of enantiomerically pure bis-methyl ester of the (S,S)-pyridine-2,6-diyl bis-alanine [J].

Basu, B ;

Frejd, T .

ACTA CHEMICA SCANDINAVICA, 1996, 50 (04) :316-322

[3]

Synthesis and catalytic activity of allyl, methallyl and methyl complexes of nickel(II) and palladium(II) with biphosphine monoxide ligands:: oligomerization of ethylene and copolymerization of ethylene and carbon monoxide [J].

Brassat, I ;

Keim, W ;

Killat, S ;

Möthrath, M ;

Mastrorilli, P ;

Nobile, CF ;

Suranna, GP .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 157 (1-2) :41-58

[4]

MODES OF COORDINATION FOR THE PHOSPHORYLIC UNIT [J].

BURFORD, N .

COORDINATION CHEMISTRY REVIEWS, 1992, 112 :1-18

[5]

Captured and cross-linked palladium nanoparticles [J].

Cho, Jin Ku ;

Najman, Romain ;

Dean, Tony W. ;

Ichihara, Osamu ;

Muller, Christophe ;

Bradley, Mark .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) :6276-6277

[6]

DEMEIJERE A, 2000, METAL CATALYZED CROS

[7]

Stereospecific palladium-catalyzed cross-coupling of (E)- and (Z)-alkenylsilanolates with aryl chlorides [J].

Denmark, Scott E. ;

Kallemeyn, Jeffrey M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) :15958-15959

[8]

Reduction of allylpalladium(II)chloride dimer by formation of allyloxysilanes [J].

Denmark, Scott E. ;

Smith, Russell C. .

SYNLETT, 2006, (18) :2921-2928

[9]

Palladium-catalyzed cross-coupling reactions of silanolates: A paradigm shift in silicon-based cross-coupling reactions [J].

Denmark, Scott. E. ;

Baird, John D. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (19) :4954-4963

[10]

Palladium-catalyzed cross-coupling reactions of heterocyclic silanolates with substituted aryl iodides and bromides [J].

Denmark, SE ;

Baird, JD .

ORGANIC LETTERS, 2006, 8 (04) :793-795

← 1 2 3 4 5 6 7 →