C(sp2)-C(sp) and C(sp)-C(sp) coupling reactions catalyzed by oxime-derived palladacycles

被引:146
作者
Alonso, DA [1 ]
Nájera, C [1 ]
Pacheco, MC [1 ]
机构
[1] Univ Alicante, Dept Quim Organ, Alicante 03080, Spain
关键词
alkynes; aryl halides; C-C coupling; homogeneous catalysis; metallacycles; N ligands; palladium;
D O I
10.1002/adsc.200303067
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Oxime-derived chloro-bridged palladacycle 8a, derived from 4,4'-dichlorobenzophenone, is an efficient pre-catalyst for the copper- and amine-free Sonogashira coupling between terminal acetylenes and aryl iodides and aryl and vinyl bromides achieving turnover numbers (TON) of up to 72000. Catalyst 8a has also been shown as a effective promoter for the sila-Sonogashira coupling between 1-(trimethylsilyl)alkynes and aryl iodides and bromides in the presence of CuI or Bu4NBr as co-catalysts. This complex also catalyzes efficiently the homocoupling reaction (Glaser-type coupling) between 1-alkynes in NMP at room temperature with TONs of up to 1000. All the reactions can be performed under air and employing reagent-grade chemicals under very low loading conditions, which demonstrates the versatility and high activity of oxime-derived palladacycles.
引用
收藏
页码:1146 / 1158
页数:13
相关论文
共 67 条