SYNTHESIS OF TRANS-ARYLVINYLBORONATES VIA A PALLADIUM-CATALYZED CROSS-COUPLING OF A VINYLBORONATE ESTER WITH ARYL HALIDES

被引：50

作者：

STEWART, SK ^{[1
]}

WHITING, A ^{[1
]}

机构：

[1] UNIV MANCHESTER,INST SCI & TECHNOL,DEPT CHEM,MANCHESTER M60 1QD,LANCS,ENGLAND

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1994年 / 482卷 / 1-2期

关键词：

PALLADIUM; ARYL HALIDES; COUPLING; BORONATE; VINYL;

D O I：

10.1016/0022-328X(94)88213-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Vinylboronate 1, protected as its pinacol ester, can be cross-coupled with aryl halides in the presence of palladium(0) to give the styrylboronate 2 as the major or exclusive product under optimized reaction conditions. The styrylboronate Heck products 2 are obtained with higher yields when aryl iodides rather than aryl bromides are used. Heteroaromatic halides are only reactive when silver(I) salts are added to the reaction mixture.

引用

页码：293 / 300

页数：8

共 16 条

[1] ROLE AND EFFECTS OF HALIDE-IONS ON THE RATES AND MECHANISMS OF OXIDATIVE ADDITION OF IODOBENZENE TO LOW-LIGATED ZEROVALENT PALLADIUM COMPLEXES PD0(PPH3)2 [J].

AMATORE, C ;

AZZABI, M ;

JUTAND, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8375-8384

[2]

CABRI W, 1992, SYNLETT, P871

[3]

Heck R. F., 1985, PALLADIUM REAGENTS O

[4] STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .23. TRANSFER OF CHIRALITY ON ADDITION OF (ALPHA-CHLOROALLYL)BORONATES TO ALDEHYDES [J].

HOFFMANN, RW ;

LANDMANN, B .

CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (06) :2013-2024

[5] SYNTHESIS OF SOME DIPHENYL AND TRIPHENYL DERIVATIVES OF ANTHRACENE AND NAPHTHALENE [J].

HOUSE, HO ;

CAMPBELL, WJ ;

KOEPSELL, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (07) :1003-&

[6] HECK VERSUS SUZUKI PALLADIUM-CATALYZED CROSS-COUPLING OF A VINYLBORONATE ESTER WITH ARYL HALIDES [J].

HUNT, AR ;

STEWART, SK ;

WHITING, A .

TETRAHEDRON LETTERS, 1993, 34 (22) :3599-3602

[7] (E)-(2-BROMOETHENYL)DIISOPROPOXYBORANE - A NEW BUILDING BLOCK FOR (E)-OLEFINS [J].

HYUGA, S ;

YAMASHINA, N ;

HARA, S ;

SUZUKI, A .

CHEMISTRY LETTERS, 1988, (05) :809-812

[8] FACILE ARYL ARYL EXCHANGE BETWEEN THE PALLADIUM CENTER AND PHOSPHINE-LIGANDS IN PALLADIUM(II) COMPLEXES [J].

KONG, KC ;

CHENG, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6313-6315

[9] DEPROTONATION OF 1,1-DIBORONIC ESTERS AND REACTIONS OF THE CARBANIONS WITH ALKYL-HALIDES AND CARBONYL-COMPOUNDS [J].

MATTESON, DS ;

MOODY, RJ .

ORGANOMETALLICS, 1982, 1 (01) :20-28

[10] THE STEREOSELECTIVE SYNTHESIS OF ALPHA, BETA-UNSATURATED KETONES BY THE STEPWISE CROSS-COUPLING REACTION OF [E]-(2-BROMOETHENYL)DIISOPROPOXYBORANE [J].

OGIMA, M ;

HYUGA, S ;

HARA, S ;

SUZUKI, A .

CHEMISTRY LETTERS, 1989, (11) :1959-1962

← 1 2 →