Palladium-catalysed synthesis of biaryl phosphines

被引：56

作者：

Baillie, C ^{[1
]}

Xiao, JL ^{[1
]}

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

来源：

TETRAHEDRON | 2004年 / 60卷 / 19期

关键词：

phosphines; Suzuki coupling; palladium catalysis; homogeneous catalysis;

D O I：

10.1016/j.tet.2004.03.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Monodentate, biphenyl-type phosphines have emerged as a powerful class of ligands in homogeneous catalysis. Synthetic methods for these ligands are limited, however. We report that the palladium-catalysed Suzuki coupling of OPR2(o-C6H4X) (R=Ph, t-Bu; X=Br, I) with arylboronic acids affords a variety of biaryl phosphine oxides including those that contain heterocycles. The corresponding phosphines are readily obtained by treatment with HSiCl3. The methodology provides an easy entry to monodentate biaryl and heterobiaryl P<^>X (X=N, O, S) phosphines with diverse steric and electronic properties. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4159 / 4168

页数：10

共 51 条

[1] Asymmetric arylation of ketone enolates [J].

Ahman, J ;

Wolfe, JP ;

Troutman, MV ;

Palucki, M ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1918-1919

[2] Synthesis of biphenyl-based phosphines by Suzuki coupling [J].

Baillie, C ;

Chen, WP ;

Xiao, JL .

TETRAHEDRON LETTERS, 2001, 42 (51) :9085-9088

[3]

BUCHWALD SL, 2001, Patent No. 6307087

[4] Palladium-catalyzed synthesis of aqueous, fluorous, and supercritical CO2-soluble phosphines [J].

Chen, WP ;

Xu, LJ ;

Xiao, JL .

ORGANIC LETTERS, 2000, 2 (17) :2675-2677

[5]

CORNILS B, 1996, APPL HONOGENEOUS CAT

[6] Stepwise formation of heterobimetallic macrocycles synthesized via the weak-link approach [J].

Eisenberg, AH ;

Ovchinnikov, MV ;

Mirkin, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2836-2837

[7] Phosphine-pyridyl and related ligands in synthesis and catalysis [J].

Espinet, P ;

Soulantica, K .

COORDINATION CHEMISTRY REVIEWS, 1999, 193-5 :499-556

[8] A negative activation energy for luminescence decay: Specific solvation effects on the emission properties of bis(2,2'-bipyridine)(3,5-dicarboxy-2,2'-bipyridine)ruthenium(II) chloride [J].

Fernando, SRL ;

Maharoof, USM ;

Deshayes, KD ;

Kinstle, TH ;

Ogawa, MY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (24) :5783-5790

[9]

Gray M, 1998, SYNLETT, P422

[10] THE EFFECT OF SOME ADDITIVES ON THE STILLE PD0-CATALYZED CROSS-COUPLING REACTION [J].

GRONOWITZ, S ;

BJORK, P ;

MALM, J ;

HORNFELDT, AB .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 460 (01) :127-129

← 1 2 3 4 5 6 →