Phosphines having a 2,3,4,5-tetraphenylphenyl moiety: Effective ligands in palladium-catalyzed transformations of aryl chlorides
Phosphines having a 2,3,4,5-tetraphenylphenyl moiety: Effective ligands in palladium-catalyzed transformations of aryl chlorides
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DOI：
10.1021/om060615q
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发表时间：
2006-09-11
期刊：
影响因子：
2.8
通讯作者：
Tsuji, Yasushi
中科院分区：
文献类型：
--
作者：
Iwasawa, Tetsuo;Komano, Tomoko;Tsuji, Yasushi
在三苯基膦的一个苯基环（邻位、间位或对位）上具有2,3,4,5-四苯基苯基（TPPh）片段的三芳基膦。其中，邻位衍生物在三种不同的钯催化反应中，即Suzuki-Miyaura偶联、Mizoroki-Heck反应和me3siisime3的硅化反应中，对未活化的芳酰氯尤其有效。另一方面，相应的元衍生物和对衍生物在这些催化反应中根本不能作为配体有效。以有效磷化氢（邻位衍生物）为配体的Pd(0)配合物的x射线晶体结构表明，TPPh上的eta(2)-配位是普遍可行的，可以实现高活性催化剂体系。
Three new triarylphosphines were prepared that have a 2,3,4,5-tetraphenylphenyl (TPPh) moiety on one of the phenyl rings (at the ortho, meta, or para position) of triphenylphosphine. Among them, the ortho derivative is particularly effective to utilize unactivated aryl chlorides in three different palladium-catalyzed reactions, i.e., Suzuki-Miyaura coupling, Mizoroki-Heck reaction, and silylation with Me3SiSiMe3. On the other hand, the corresponding meta and para derivatives are not effective as ligands at all in these catalytic reactions. X-ray crystal structures of Pd(0) complexes having the effective phosphines (ortho derivatives) as ligands show that eta(2)-coordination on the TPPh moiety is general and operative to realize a highly active catalyst system.