An inexpensive and highly stable ligand 1,4-bis(2-hydroxy-3,5-di-tert-butylbenzyl)piperazine for Mizoroki-Heck and room temperature Suzuki-Miyaura cross-coupling reactions

被引：69

作者：

Mohanty, Sasmita ^{[1
]}

Suresh, D. ^{[1
]}

Balakrishna, Maravanji S. ^{[1
]}

Mague, Joel. T. ^{[2
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

[2] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA

来源：

TETRAHEDRON | 2008年 / 64卷 / 01期

关键词：

oxygen donor ligands; nitrogen donor; palladium complex; catalysis; suzuki cross-coupling; Mizoroki-Heck reactions;

D O I：

10.1016/j.tet.2007.10.081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A bulky, inexpensive and simple bidentate ligand 1,4-bis(2-hydroxy-3,5-di-tert-butylbenzyl)piperazine (1) has been synthesized and characterized. The palladium catalyst was formed by combination of 1 with [Cl2Pd(COD)] in a ratio of 1:1, tested in the Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions. Coupling of a variety of aryl bromides with phenylboronic acid using methanol as solvent at room temperature, or at 60 degrees C, gave aenerally high yields of coupled products. Coupling of aryl chlorides with organoboron reagent at 110 degrees C in DMF afforded good yields of biaryls under aerobic conditions. This non-phosphorus, air and moisture stable catalyst also displays good activity for Mizoroki-Heck coupling reaction in methanol at 60 degrees C with various aryl chlorides and bromides. (c) 2007 Elsevier Ltd. All fights reserved.

引用

页码：240 / 247

页数：8

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