Synthesis of arylboronates via the palladium(O)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates

被引：320

作者：

Ishiyama, T ^{[1
]}

Itoh, Y ^{[1
]}

Kitano, T ^{[1
]}

Miyaura, N ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC ENGN,DIV MOL CHEM,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(97)00642-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cross-coupling reaction of (RO)(2)BB(OR)(2) (RO = methoxo and pinacolato) with aryl triflates to give arylboronates was carried out at 80 degrees C in the presence of PdCl2(dppf) (3 mol%), dppf (3 mol%) and KOAc (3 equivs) in dioxane. The reaction was available with various functional groups such as nitro, cyano, ester, and carbonyl groups. (C) 1997 Elsevier Science Ltd.

引用

页码：3447 / 3450

页数：4

共 17 条

[1]

ABRAHAM MH, 1985, CHEM METAL CARBON BO, V2, P25

[2] TRANSITION-METAL-CATALYZED DIBORATION OF VINYLARENES [J].

BAKER, RT ;

NGUYEN, P ;

MARDER, TB ;

WESTCOTT, SA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (12) :1336-1338

[3] Platinum(0)-catalyzed diboration of alkynes with tetrakis(alkoxo)diborons: An efficient and convenient approach to cis-bis(boryl) alkenes [J].

Ishiyama, T ;

Matsuda, N ;

Murata, M ;

Ozawa, F ;

Suzuki, A ;

Miyaura, N .

ORGANOMETALLICS, 1996, 15 (02) :713-720

[4] A synthesis of allylboronates via the palladium(0)-catalyzed cross-coupling reaction of bis(pinacolato)diboron with allylic acetates [J].

Ishiyama, T ;

Ahiko, T ;

Miyaura, N .

TETRAHEDRON LETTERS, 1996, 37 (38) :6889-6892

[5] PLATINUM(O)-CATALYZED DIBORATION OF ALKYNES [J].

ISHIYAMA, T ;

MATSUDA, N ;

MIYAURA, N ;

SUZUKI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11018-11019

[6] PALLADIUM(O)-CATALYZED CROSS-COUPLING REACTION OF ALKOXYDIBORON WITH HALOARENES - A DIRECT PROCEDURE FOR ARYLBORONIC ESTERS [J].

ISHIYAMA, T ;

MURATA, M ;

MIYAURA, N .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7508-7510

[7]

ISHIYAMA T, IN PRESS J CHEM SOC

[8]

ISHIYAMA T, 1996, J CHEM SOC CHEM COMM, P2073

[9] Mechanistic investigation of stoichiometric alkyne insertion into Pt-B bonds and related chemistry bearing on the catalytic diborylation of alkynes mediated by platinum(II) diboryl complexes [J].

Iverson, CN ;

Smith, MR .

ORGANOMETALLICS, 1996, 15 (24) :5155-5165

[10] REACTIVITY OF ORGANOPLATINUM COMPLEXES WITH C6H4O2B-BO2C6H4 - SYNTHESES OF A PLATINUM DIBORYL COMPLEX WITH, AND WITHOUT, METATHESIS OF BORON BORON AND METAL-CARBON BONDS [J].

IVERSON, CN ;

SMITH, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (15) :4403-4404

← 1 2 →