Cross-coupling of alkynylsilanols with aryl halides promoted by potassium trimethylsilanolate

被引:44
作者
Denmark, SE [1 ]
Tymonko, SA [1 ]
机构
[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
关键词
D O I
10.1021/jo0351771
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed cross-coupling of aliphatic alkynylsilanols with aryl iodides has been demonstrated with potassium trimethylsilanolate as the coupling promoter and copper(I) iodide as a cocatalyst. The cross-coupling proceeds at room temperature in good to excellent yield with a range of aryl iodides. A comparison of the reactivity of alkynylsilanols, trimethylsilylalkynes, and terminal alkynes under fluoride and fluoride-free conditions was per-formed to elucidate the role of silicon in the Sonogashira reaction.
引用
收藏
页码:9151 / 9154
页数:4
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