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Copper-free and amine-free Sonogashira coupling in air in a mixed aqueous medium by palladium complexes of N/O-functionalized N-heterocyclic carbenes

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Title Copper-free and amine-free Sonogashira coupling in air in a mixed aqueous medium by palladium complexes of N/O-functionalized N-heterocyclic carbenes
 
Creator SAMANTARAY, MK
SHAIKH, MM
GHOSH, P
 
Subject ring-opening polymerization
crystal-structure
aryl chlorides
fischer-type
organometallic compounds
nucleophilic-addition
iminocarbene ligands
terminal acetylenes
vibrational-spectra
catalytic-activity
carbenes
functionalized nhc
sonogashira coupling
organometallic catalysis
palladium-nhc complex
 
Description Highly convenient copper-free and amine-free Sonogashira coupling of aryl bromides and iodides with terminal acetylenes under amenable conditions in air and in a mixed aqueous medium are reported using several new, user friendly and robust palladium precatalysts (1-5) of N/O-functionalized N-heterocyclic carbenes (NHCs). In particular, the precatalysts, 1 and 2, were synthesized from the imidazolium chloride salts by the treatment with PdCl(2) in pyridine in presence of K(2)CO(3) as a base while the precatalysts, 3-5, were synthesized from the respective silver complexes by the treatment with (COD) PdCl(2). The DFT studies carried out on the 1-5 complexes suggest the presence of strong NHC-Pd sigma-interactions arising out of deeply buried NHC-Pd sigma-bonding molecular orbitals (MOs) that account for the inert nature of the metal-carbene bonds and also provide insights into the exceptional stability of these precatalysts. (C) 2009
 
Publisher ELSEVIER SCIENCE SA
 
Date 2011-07-27T18:26:02Z
2011-12-26T12:57:58Z
2011-12-27T05:46:36Z
2011-07-27T18:26:02Z
2011-12-26T12:57:58Z
2011-12-27T05:46:36Z
2009
 
Type Article
 
Identifier JOURNAL OF ORGANOMETALLIC CHEMISTRY, 694(21), 3477-3486
0022-328X
http://dx.doi.org/10.1016/j.jorganchem.2009.06.026
http://dspace.library.iitb.ac.in/xmlui/handle/10054/7297
http://hdl.handle.net/10054/7297
 
Language en