Synthesis of bicyclic enediynes from bis[phenyl[(trifluoromethanesulfonyl)oxy]iodo]acetylene: A tandem Diels-Alder/palladium(II)- and copper(I)-cocatalyzed cross-coupling approach

被引：42

作者：

Ryan, JH ^{[1
]}

Stang, PJ ^{[1
]}

机构：

[1] UNIV UTAH,DEPT CHEM,SALT LAKE CITY,UT 84112

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 18期

关键词：

D O I：

10.1021/jo960750k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of bicycle alkenylbis(phenyliodonium) triflates 1a or b (available via the Diels-Alder reaction of bis[phenyl[(trifluoromethanesulfonyl)oxy]iodo]acetylene with cyclopentadiene or furan, respectively) with alkynylstannanes 2a-g at room temperature in DMF in the presence of catalytic amounts of trans-benzyl(chloro)bis(triphenylphosphine)palladium(II) and copper(I) iodide proceeds smoothly and with selectivity to afford good to excellent yields of bicyclic enediynes 3a-k.

引用

页码：6162 / 6165

页数：4

共 60 条

[1]

ABRAHAM RJ, 1978, PROTON CARBON 13 NMR

[2] CONVENIENT ONE-POT SYNTHESIS OF FUNCTIONALIZED UNSYMMETRICAL (Z)-ENEDIYNES OR (E)-ENEDIYNES FROM (Z)-1,2-DICHLOROETHYLENE OR (E)-1,2-DICHLOROETHYLENE - AN EFFICIENT ROUTE TO (Z,Z,Z) AND (Z,E,Z)-TRIENES [J].