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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/100/13823

Title: Selenoether ligand assisted Heck catalysis
Authors: CHAKRABORTY, T
SRIVASTAVA, K
SINGH, HB
BUTCHER, RJ
Keywords: CROSS-COUPLING REACTIONS
N-HETEROCYCLIC CARBENES
PALLADIUM(II) COMPLEXES
ARYL CHLORIDES
EFFICIENT LIGAND
SPECTROSCOPY
PLATINUM(II)
PALLADACYCLES
DERIVATIVES
CHEMISTRY
Issue Date: 2011
Publisher: ELSEVIER SCIENCE SA
Citation: JOURNAL OF ORGANOMETALLIC CHEMISTRY,696(13)2559-2564
Abstract: 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.
URI: http://dx.doi.org/10.1016/j.jorganchem.2011.03.047
http://dspace.library.iitb.ac.in/jspui/handle/100/13823
ISSN: 0022-328X
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