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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

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Title 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
 
Creator MOHANTY, SASMITA
SURESH, D
BALAKRISHNA, MS
MAGUE, JOEL T
 
Subject oxygen donor ligands
nitrogen donor
palladium compounds
catalysis
suzuki cross-coupling
mizoroki-heck reactions
 
Description 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 °C, gave generally high yields of coupled products. Coupling of aryl chlorides with organoboron reagent at 110 °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 °C with various aryl chlorides and bromides.
 
Publisher Elsevier
 
Date 2009-03-20T05:58:02Z
2011-11-25T19:48:53Z
2011-12-26T13:07:51Z
2011-12-27T05:55:50Z
2009-03-20T05:58:02Z
2011-11-25T19:48:53Z
2011-12-26T13:07:51Z
2011-12-27T05:55:50Z
2008
 
Type Article
 
Identifier Tetrahedron 64(1), 240-247
0040-4020
http://dx.doi.org/10.1016/j.tet.2007.10.081
http://hdl.handle.net/10054/1025
http://dspace.library.iitb.ac.in/xmlui/handle/10054/1025
 
Language en