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Selenoether ligand assisted Heck catalysis

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Title Selenoether ligand assisted Heck catalysis
 
Creator CHAKRABORTY, T
SRIVASTAVA, K
SINGH, HB
BUTCHER, RJ
 
Subject CROSS-COUPLING REACTIONS
N-HETEROCYCLIC CARBENES
PALLADIUM(II) COMPLEXES
ARYL CHLORIDES
EFFICIENT LIGAND
SPECTROSCOPY
PLATINUM(II)
PALLADACYCLES
DERIVATIVES
CHEMISTRY
Selenoether
Selenide
Heck reaction
Palladium
 
Description Selenoether ligands, 2,2'-methylenebis(selanediyl)bis(2,1-phenylene)dimethanol (5), (2,2'-(ethane-1,2-diylbis(selanediyl))bis(2,1-phenylene))dimethanol (6) and (2-(benzylselanyl)phenyl)methanol (7) have been synthesized by reducing di-o-formylphenyl diselenide and reacting the in situ generated selenolate with dibromomethane, 1,2-dibromoethane and benzyl chloride, respectively. The ligands, bis(2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenylselanyl)methane (8) and 1,2-bis(2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenylselanyl)ethane (9) have been synthesized similarly from bis[2-(4,4-dimethyl-2-oxazolinyl)phenyl] diselenide using electrophiles dibromomethane and 1,2-dibromoethane, respectively. Activity of ligands 5-9 along with 2-(2-(benzylselanyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole (10) and 1-(2-(benzylselanyl)phenyl)-N,N-dimethylmethanamine (11) were examined for the Heck reaction of aryl halides with olefins. Bidentate Se,N ligand 11 was found to be the best one in the series and constitutes an efficient phosphine-free catalytic system with PdCl(2). The catalytic system showed moderate activity for the coupling of activated aryl chlorides in the presence of tetra-n-butyl ammonium bromide (TBAB). Complexes [10-PdCl(2)] (12) and [11-PdCl(2)] (13) have shown marginally better activity in comparison to the in situ generated catalysts from PdCl(2) and 10 and 11, respectively in the coupling of 4-bromoacetophenone with n-butylacrylate. Ligand 9 and complex 13 have been characterized by single crystal X-ray diffraction analysis. (C) 2011 Elsevier B.V. All rights reserved.
 
Publisher ELSEVIER SCIENCE SA
 
Date 2012-01-20T10:09:44Z
2012-01-20T10:09:44Z
2011
 
Type Article
 
Identifier JOURNAL OF ORGANOMETALLIC CHEMISTRY,696(13)2559-2564
0022-328X
http://dx.doi.org/10.1016/j.jorganchem.2011.03.047
http://dspace.library.iitb.ac.in/jspui/handle/100/13823
 
Language English