Palladium-catalysed cross coupling of arylboronic acids with 2-chloro-1,4-naphthoquinones: the synthesis of 2-aryl- and 2,3-bisaryl-1,4-naphthoquinones

被引：24

作者：

Best, WM ^{[1
]}

Sims, CG ^{[1
]}

Winslade, M ^{[1
]}

机构：

[1] Chem Ctr WA, Perth, WA 6004, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2001年 / 54卷 / 06期

关键词：

D O I：

10.1071/CH01024

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-Chloro-1,4-naphthoquinones underwent palladium-catalysed cross coupling reactions with arylboronic acids to give the corresponding 2-aryl-1,4-naphthoquinones. Similarly, 2,3-dichloro-1,4-naphthoquinone underwent efficient cross coupling reactions with arylboronic acids to give mono or bis adducts. The required 2-chloro-1,4-naphthoquinones were conveniently prepared from the corresponding 2-hydroxy-1,4-naphthoquinones by treatment with oxalyl chloride.

引用

收藏

页码：401 / 404

页数：4

相关论文

共 26 条

[1] QUINOL IMIDE ACETATES .3. ADDITION REACTIONS OF 2-METHYL-ORTHO-NAPHTHOQUINOL-PARA-TOLUENESULFONIMIDE ACETATE [J].

ADAMS, R ;

DUNBAR, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (18) :4774-4778

[2] Constituents of Conospermum brachyphyllum.: Improved methods for the isolation and synthesis of (+)-conocurvone and the structure of (+)-brachyphyllone [J].

Armstrong, JA ;

Baker, RW ;

Best, WM ;

Byrne, LT ;

Cannon, JR ;

Colegate, SM ;

Gray, AR ;

Marchant, NG ;

Rothnie, N ;

Sargent, MV ;

Sims, CG ;

Spadek, ZE ;

Trengove, RD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (01) :57-62

[3] QUINONES .7. NEW ROUTES TO 2-HYDROXY-1,4-NAPHTHAQUINONES [J].

BAILLIE, AC ;

THOMSON, RH .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (23) :2184-&

[4]

BUZBEE LR, Patent No. 1128115

[5]

CLARK RD, 1974, SYNTHESIS-STUTTGART, P47

[6] CONCISE SYNTHESIS OF BELAMCANDAQUINONE-A AND BELAMCANDAQUINONE-B BY PALLADIUM (0) CATALYZED CROSS-COUPLING REACTION OF BROMOQUINONE WITH ARYLBORONIC ACIDS [J].

FUKUYAMA, Y ;

KIRIYAMA, Y ;

KODAMA, M .

TETRAHEDRON LETTERS, 1993, 34 (47) :7637-7638

[7]

GUPTA RB, 1990, SYNLETT, P355

[8] NOVEL SYNTHESIS OF ISOFLAVONES BY THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 3-BROMOCHROMONES WITH ARYLBORONIC ACIDS OR ITS ESTERS [J].

HOSHINO, Y ;

MIYAURA, N ;

SUZUKI, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (08) :3008-3010

[9] 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

[10]

KATSUMURA S, Patent No. 09077743