使用大位阻钯-菲基咪唑鎓卡宾催化的Sonogashira偶联反应。

Sonogashira coupling using bulky palladium-phenanthryl imidazolium carbene catalysis.

作者信息

Ma Yudao, Song Chun, Jiang Wei, Wu Quansheng, Wang Yong, Liu Xueying, Andrus Merritt B

机构信息

Brigham Young University, Department of Chemistry and Biochemistry, C100 BNSN, Provo, Utah 84602-5700, USA.

出版信息

Org Lett. 2003 Sep 4;5(18):3317-9. doi: 10.1021/ol035147k.

DOI:10.1021/ol035147k

PMID:12943416

Abstract

[structure: see text] Bulky phenanthracenyl imidazolium-derived carbene ligands were investigated for copper-free Sonogashira coupling with terminal acetylenes. Aryl bromides and iodides gave coupled products in excellent yields from the Pd(PPh(3))(2)Cl(2) complex with potassium t-butoxide and 18-crown-6 in THF. A remarkable dependence on the size of the ligand was found. The highest yields were obtained with the bulky 2,9-dicyclohexyl-10-phenanthryl ligand 5.

摘要

[结构：见正文] 研究了体积较大的菲基咪唑鎓衍生卡宾配体用于与末端乙炔进行无铜Sonogashira偶联反应。在四氢呋喃中，芳基溴化物和碘化物与钯（II）二（三苯基膦）二氯化物、叔丁醇钾和18-冠-6形成的配合物反应，能以优异的产率得到偶联产物。发现产率对配体大小有显著依赖性。使用体积较大的2,9-二环己基-10-菲基配体5时获得了最高产率。