A PALLADIUM-CATALYZED CYCLIZATION-CARBONYLATION-COUPLING REACTION BETWEEN ARYL HALIDES AND GAMMA-HYDROXYALLENES TO FORM ARYL (TETRAHYDROFURAN-2-YL)VINYL KETONES

被引：50

作者：

WALKUP, RD

GUAN, LF

KIM, YS

KIM, SW

机构：

[1] Department of Chemistry and Biochemistry, Texas Tech University, Lubbock

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 22期

关键词：

D O I：

10.1016/0040-4039(95)00666-Z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

gamma-Hydroxyallenes undergo cyclization-carbonylation-coupling with aryl (and one alkenyl) halides in the presence of catalytic Pd(PPh(3))(4), base, and CO to form the title ketones in good yields. The reaction was temperature dependent: at 80 degrees C, the CO insertion did not readily occur, while at 55-60 degrees C the ketone products predominated. Yields for the Pd(O)-catalyzed cyclization-coupling reaction (without insertion) improved when tert-butyl isocyanide was added (with no CO present), implying that a good pi acid ligand improves the cyclization-coupling reactions between arylpalladium(II) halides and gamma-hydroxyallenes.

引用

页码：3805 / 3808

页数：4

共 11 条

[1] PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES AND VINYL ARYL HALIDES WITH 4-ALKYNOIC ACIDS - REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (E)-DELTA-VINYL ARYL-GAMMA-METHYLENE-GAMMA-BUTYROLACTONES [J].