%0 Journal Article %1 ISI:000335516900015 %A Sabounchei, Seyyed Javad %A Pourshahbaz, Mahbubeh %A Hashemi, Ali %A Ahmadi, Mohsen %A Karamian, Roya %A Asadbegy, Mostafa %A Khavasi, Hamid Reza %C PO BOX 564, 1001 LAUSANNE, SWITZERLAND %D 2014 %I ELSEVIER SCIENCE SA %J JOURNAL OF ORGANOMETALLIC CHEMISTRY %K Antibacterial Crystal Low Phosphorus Suzuki agent} catalyst complex; cross-coupling; loading; structure; ylide; {Cu(I) %P 111-119 %R 10.1016/j.jorganchem.2014.03.017 %T Synthesis and structural characterization of dimeric phosphine ylide Cu(I) complexes: Application in Suzuki cross-coupling reactions and biological evaluation as antibacterial agents %V 761 %X In this work we report the synthesis of the complexes of the type Cu(mu-Cl)\Ph2P(CH2)(n)PPh2C(H)C(O) PhR\(2) (n = 1: R = Cl (1), NO2 (2); n = 2: R = Cl (3), NO2 (4)) derived from the reactions of the copper(I) chloride with related phosphorus ylides in equimolar ratios using dry methanol as solvent. The identity of complex 1 was unequivocally determined by single crystal X-ray diffraction techniques, its structure consisting of five-membered rings formed by coordination of the ligands through the phosphine group and the ylidic carbon atom to the metal center. The coordination geometry around the Cu atoms in this complex can be defined as slightly distorted tetrahedral. Characterization of the obtained compounds was also performed by IR, H-1, P-31 and C-13 NMR spectroscopy and analytical data indicated a 1: 1 stoichiometry between the Cu(I) chloride and ylide. Well-defined phosphine bis-ylide Cu(I) complexes 1 and 3 were found to be an effective catalyst for the Suzuki coupling of various aryl halides including with 4-ethyl phenylboronic acid, giving the desired coupling products at low catalyst loading in moderate to good yields. Also, the antibacterial activities of DMSO-solved complexes were measured by disc diffusion method against 6 Gram positive and negative bacteria. All Cu(I) complexes exhibited antibacterial activities against bacteria tested especially Gram negative ones. (C) 2014 Elsevier B.V. All rights reserved.

@article{ISI:000335516900015, abstract = {{In this work we report the synthesis of the complexes of the type {[}Cu(mu-Cl)\{Ph2P(CH2)(n)PPh2C(H)C(O) PhR\}](2) (n = 1: R = Cl (1), NO2 (2); n = 2: R = Cl (3), NO2 (4)) derived from the reactions of the copper(I) chloride with related phosphorus ylides in equimolar ratios using dry methanol as solvent. The identity of complex 1 was unequivocally determined by single crystal X-ray diffraction techniques, its structure consisting of five-membered rings formed by coordination of the ligands through the phosphine group and the ylidic carbon atom to the metal center. The coordination geometry around the Cu atoms in this complex can be defined as slightly distorted tetrahedral. Characterization of the obtained compounds was also performed by IR, H-1, P-31 and C-13 NMR spectroscopy and analytical data indicated a 1: 1 stoichiometry between the Cu(I) chloride and ylide. Well-defined phosphine bis-ylide Cu(I) complexes 1 and 3 were found to be an effective catalyst for the Suzuki coupling of various aryl halides including with 4-ethyl phenylboronic acid, giving the desired coupling products at low catalyst loading in moderate to good yields. Also, the antibacterial activities of DMSO-solved complexes were measured by disc diffusion method against 6 Gram positive and negative bacteria. All Cu(I) complexes exhibited antibacterial activities against bacteria tested especially Gram negative ones. (C) 2014 Elsevier B.V. All rights reserved.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{PO BOX 564, 1001 LAUSANNE, SWITZERLAND}}, affiliation = {{Sabounchei, SJ (Reprint Author), Bu Ali Sina Univ, Fac Chem, Hamadan 65174, Iran. Sabounchei, Seyyed Javad; Pourshahbaz, Mahbubeh; Hashemi, Ali; Ahmadi, Mohsen, Bu Ali Sina Univ, Fac Chem, Hamadan 65174, Iran. Karamian, Roya; Asadbegy, Mostafa, Bu Ali Sina Univ, Dept Biol, Fac Sci, Hamadan 65174, Iran. Khavasi, Hamid Reza, Shahid Beheshti Univ, Dept Chem, GC, Tehran 1983963113, Iran.}}, author = {Sabounchei, Seyyed Javad and Pourshahbaz, Mahbubeh and Hashemi, Ali and Ahmadi, Mohsen and Karamian, Roya and Asadbegy, Mostafa and Khavasi, Hamid Reza}, author-email = {{jsabounchei@yahoo.co.uk}}, biburl = {https://www.bibsonomy.org/bibtex/2d7b8181e9e7edcff877ad151aea20d83/hkhavasi}, cited-references = {{Alonso F, 2008, TETRAHEDRON, V64, P3047, DOI 10.1016/j.tet.2007.12.036. Aslanidis P, 2002, INORG CHEM, V41, P6875, DOI 10.1021/ic025896i. BAUER AW, 1966, AM J CLIN PATHOL, V45, P493. Bokach NA, 2003, INORG CHEM, V42, P3602, DOI 10.1021/ic034086j. BRINGMANN G, 1990, ANGEW CHEM INT EDIT, V29, P977, DOI 10.1002/anie.199009771. Chen HP, 2005, J CHIN CHEM SOC-TAIP, V52, P687. Christau H. J., 1994, CHEM REV, V94, P1299. Creaven BS, 2006, INORG CHIM ACTA, V359, P3976, DOI 10.1016/j.ica.2006.04.006. Diederich F., 2004, METAL CATALYZED CROS. 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YAMAMOTO Y, 1975, J ORGANOMET CHEM, V96, P133, DOI 10.1016/S0022-328X(00)86429-3. Yang CT, 2011, ANGEW CHEM INT EDIT, V50, P3904, DOI 10.1002/anie.201008007. Yong B.S., 2003, CHEMTRACTS ORG CHEM, P205. Yuan YF, 2001, INORG CHIM ACTA, V324, P309, DOI 10.1016/S0020-1693(01)00661-2.}}, doc-delivery-number = {{AG6GK}}, doi = {{10.1016/j.jorganchem.2014.03.017}}, eissn = {{1872-8561}}, funding-acknowledgement = {{Bu-Ali Sina University}}, funding-text = {{We are grateful to the Bu-Ali Sina University for a grant.}}, interhash = {9352723f87b76e701fd838f0347a2772}, intrahash = {d7b8181e9e7edcff877ad151aea20d83}, issn = {{0022-328X}}, journal = {{JOURNAL OF ORGANOMETALLIC CHEMISTRY}}, journal-iso = {{J. Organomet. Chem.}}, keywords = {Antibacterial Crystal Low Phosphorus Suzuki agent} catalyst complex; cross-coupling; loading; structure; ylide; {Cu(I)}, keywords-plus = {{STABILIZED PHOSPHORUS YLIDES; RAY CRYSTAL-STRUCTURE; BINUCLEAR MERCURY(II) COMPLEXES; PD(II) COMPLEXES; ARYLBORONIC ACIDS; HALIDE-COMPLEXES; PALLADIUM(II) COMPLEXES; ANTIMICROBIAL ACTIVITY; ORGANOBORON COMPOUNDS; COPPER(I) COMPLEXES}}, language = {{English}}, month = {{JUL 1}}, number-of-cited-references = {{81}}, pages = {{111-119}}, publisher = {{ELSEVIER SCIENCE SA}}, research-areas = {{Chemistry}}, times-cited = {{8}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Synthesis and structural characterization of dimeric phosphine ylide Cu(I) complexes: Application in Suzuki cross-coupling reactions and biological evaluation as antibacterial agents}}, type = {{Article}}, unique-id = {{ISI:000335516900015}}, usage-count-last-180-days = {{2}}, usage-count-since-2013 = {{46}}, volume = {{761}}, web-of-science-categories = {{Chemistry, Inorganic \& Nuclear; Chemistry, Organic}}, year = {{2014}} }