A novel and efficient route to (E)-alk-1-enyl boronic acid derivatives from (E)-1-(trimethylsilyl)alk-1-enes and a formal Suzuki-Miyaura cross-coupling reaction starting with vinylsilanes

被引：38

作者：

Farinola, GM ^{[1
]}

Fiandanese, V ^{[1
]}

Mazzone, L ^{[1
]}

Naso, F ^{[1
]}

机构：

[1] UNIV BARI,CTR CNR STUDIO METOL INNOVAT SINTESI ORGAN,DIPARTIMENTO CHIM,I-70126 BARI,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 24期

关键词：

D O I：

10.1039/C39950002523

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel and highly efficient conversion of vinylsilanes into vinyl boronates is described together with their Suzuki-Miyaura cross-coupling reaction, performed without isolating the intermediate resulting from borodesilylation.

引用

页码：2523 / 2524

页数：2

共 33 条

[1] PALLADIUM-CATALYZED DIASTEREOSELECTIVE SYNTHESES OF (E)-1-TRIMETHYLSILYL-2-ALKENES, (E)-1-TRIMETHYLSILYL-1-ALKEN-3-YNES, (1E,5E)-1-TRIMETHYLSILYL-1,5-ALKADIEN-3-YNES, (1E,3Z)- AND (1E,3E)-1-TRIMETHYLSILYL-1,3-ALKADIENES [J].

ANDREINI, BP ;

CARPITA, A ;

ROSSI, R ;

SCAMUZZI, B .

TETRAHEDRON, 1989, 45 (17) :5621-5640

[2] A NEW STRAIGHTFORWARD AND GENERAL-APPROACH TO DIENAMIDE NATURAL-PRODUCTS [J].

BABUDRI, F ;

FIANDANESE, V ;

NASO, F ;

PUNZI, A .

TETRAHEDRON LETTERS, 1994, 35 (13) :2067-2070

[3] CONJUGATED POLYENE SYNTHESIS VIA DISILYL DERIVATIVES - A DIRECT ACCESS TO OSTOPANIC ACID, A PLANT ANTICANCER AGENT, AND TO (6E)-LTB3 LEUKOTRIENE [J].

BABUDRI, F ;

FIANDANESE, V ;

NASO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6245-6248

[4]

BABUDRI F, 1992, SYNLETT, P221

[5] A GENERAL-APPROACH TO CONJUGATED (E,E)-DIENES THROUGH SEQUENTIAL COUPLING REACTIONS [J].

BABUDRI, F ;

FIANDANESE, V ;

MAZZONE, L ;

NASO, F .

TETRAHEDRON LETTERS, 1994, 35 (47) :8847-8850

[6] A NEW APPROACH TO SILYLATED KETONES AND DICARBONYL-COMPOUNDS WITH A CONJUGATED (ALL-E) DIENE OR TRIENE STRUCTURE [J].

BABUDRI, F ;

FIANDANESE, V ;

MARCHESE, G ;

NASO, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (04) :237-239

[7] HYDROBORATION .41. HYDROBORATION OF ALKENES AND ALKYNES WITH DICHLOROBORANE ETHERATES - CONVENIENT PROCEDURES FOR PREPARATION OF ALKYLDICHLOROBORANES AND ALKENYLDICHLOROBORANES AND THEIR DERIVATIVES [J].

BROWN, HC ;

RAVINDRAN, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (07) :1798-1806

[8] CATECHOLBORANE (1,3,2-BENZODIOXABOROLE) AS A NEW, GENERAL MONOHYDROBORATION REAGENT FOR ALKYNES - CONVENIENT SYNTHESIS OF ALKENEBORONIC ESTERS AND ACIDS FROM ALKYNES VIA HYDROBORATION [J].

BROWN, HC ;

GUPTA, SK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (12) :4370-&

[9] REACTION OF ALKYNES WITH DICHLOROBORANE ETHYL ETHERATE IN PRESENCE OF BORON TRICHLORIDE - SIMPLE, GENERAL SYNTHESIS OF ALKENYLDICHLOROBORANES [J].

BROWN, HC ;

RAVINDRA.N .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 61 (01) :C5-C7

[10]

Colvin E. W., 1988, SILICON REAGENTS ORG

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