Suzuki-Miyaura coupling of alkynylboronic esters generated in situ from acetylenic derivatives

被引：44

作者：

Castanet, AS

Colobert, F

Schlama, T

机构：

[1] ECPM, Lab stereochim, F-67087 Strasbourg 2, France

[2] Rhodia Rech, Ctr Recy Lyon, F-69192 St Fons, France

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 23期

关键词：

D O I：

10.1021/ol006439d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new effective Suzuki-Miyaura coupling reaction between alkynylboronic esters (generated in situ from acetylenic derivatives) and arylbromides or vinylbromides is reported.

引用

页码：3559 / 3561

页数：3

共 16 条

[1] ORGANOBORANES .31. A SIMPLE PREPARATION OF BORONIC ESTERS FROM ORGANO-LITHIUM REAGENTS AND SELECTED TRIALKOXYBORANES [J].

BROWN, HC ;

COLE, TE .

ORGANOMETALLICS, 1983, 2 (10) :1316-1319

[2] A SIMPLE, GENERAL-SYNTHESIS OF 1-ALKYNYLDIISOPROPOXYBORANES [J].

BROWN, HC ;

BHAT, NG ;

SREBNIK, M .

TETRAHEDRON LETTERS, 1988, 29 (22) :2631-2634

[3] ORGANOBORANES .38. A FACILE AND HIGHLY EFFICIENT ADDITION OF B-1-ALKYNYL-9-BORABICYCLO[3.3.1]NONANES TO ALDEHYDES AND KETONES - AN EXCEPTIONALLY CHEMOSELECTIVE SYNTHESIS OF PROPARGYLIC ALCOHOLS [J].

BROWN, HC ;

MOLANDER, GA ;

SINGH, SM ;

RACHERLA, US .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1577-1582

[4] HIGHLY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES PROMOTED BY CHIRAL OXAZABOROLIDINES [J].

COREY, EJ ;

CIMPRICH, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3151-3152

[5] PALLADIUM-CATALYZED ARYLATION OF POLAR ORGANOMETALLICS MEDIATED BY 9-METHOXY-9-BORABICYCLO[3.3.1]NONANE - SUZUKI REACTIONS OF EXTENDED SCOPE [J].

FURSTNER, A ;

SEIDEL, G .

TETRAHEDRON, 1995, 51 (41) :11165-11176

[6] NEW STEREOSPECIFIC CROSS-COUPLING BY THE PALLADIUM-CATALYZED REACTION OF 1-ALKENYLBORANES WITH 1-ALKENYL OR 1-ALKYNYL HALIDES [J].

MIYAURA, N ;

YAMADA, K ;

SUZUKI, A .

TETRAHEDRON LETTERS, 1979, 20 (36) :3437-3440

[7] NOVEL AND CONVENIENT METHOD FOR THE STEROSPECIFIC AND REGIOSPECIFIC SYNTHESIS OF CONJUGATED ALKADIENES AND ALKENYNES VIA THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH BROMOALKENES AND BROMOALKYNES [J].

MIYAURA, N ;

YAMADA, K ;

SUGINOME, H ;

SUZUKI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (04) :972-980

[8] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYLBORONIC ACID WITH HALOARENES IN THE PRESENCE OF BASES [J].

MIYAURA, N ;

YANAGI, T ;

SUZUKI, A .

SYNTHETIC COMMUNICATIONS, 1981, 11 (07) :513-519

[9]

PELTER A, 1988, BORANE REAGENTS BEST, pCH2

[10] RATES AND REGIOSELECTIVITIES OF THE PALLADIUM-CATALYZED ETHYNYLATION OF SUBSTITUTED BROMOBENZENES AND DIBROMOBENZENES [J].

SINGH, R ;

JUST, G .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) :4453-4457

← 1 2 →