%0 Journal Article %1 ISI:000311680100030 %A Sabounchei, Seyyed Javad %A Panahimehr, Mohammad %A Ahmadi, Mohsen %A Nasri, Zahra %A Khavasi, Hamid Reza %C PO BOX 564, 1001 LAUSANNE, SWITZERLAND %D 2013 %I ELSEVIER SCIENCE SA %J JOURNAL OF ORGANOMETALLIC CHEMISTRY %K Crystal Suzuki catalyst; cross-coupling reaction} structure; {Palladium %P 207-213 %R 10.1016/j.jorganchem.2012.10.004 %T Four-coordinate Pd(II) complexes containing non-symmetric phosphorus ylides: Synthesis, characterization, and catalytic behavior towards Suzuki reaction %V 723 %X In this paper it is reported the synthesis of the complexes of the type \Ph2PCH2PPh2CH=C(O)RPdCl2\ (R=4'-biphenyl (1), OCH2Ph (2), 4-methylphenyl (3), 2-naphtyl (4), 2,4-dichlorophenyl (5), 3-nitrophenyl (6)) derived from the reactions of the dichloro(1,5-cyclooctadiene)palladium(II) with related phosphorus ylides in dichloromethane under mild conditions. These compound have been characterized by, elemental analysis and spectroscopic methods. The structure of complex 1 has been characterized crystallographically. This structure consists of five-membered ring formed by coordination of the ligand through the phosphine group and the ylidic carbon atom to the metal center. The coordination geometry around the Pd atoms in this complex can be defined as slightly distorted square planar. At a supramolecular level C -H center dot center dot center dot Cl and C-H center dot center dot center dot pi intermolecular interactions are responsible for the crystal packing. This complex has been found to act as efficient catalysts for the Suzuki cross-coupling reaction. Various aryl bromides were coupled with aryl boronic acids in DMF, under air, in the presence of 0.2 mol\% of the catalyst to afford corresponding cross- coupled products in good to excellent yields. (C) 2012 Elsevier B.V. All rights reserved.

@article{ISI:000311680100030, abstract = {{In this paper it is reported the synthesis of the complexes of the type \{{[}Ph2PCH2PPh2CH=C(O)R]PdCl2\} (R=4'-biphenyl (1), OCH2Ph (2), 4-methylphenyl (3), 2-naphtyl (4), 2,4-dichlorophenyl (5), 3-nitrophenyl (6)) derived from the reactions of the dichloro(1,5-cyclooctadiene)palladium(II) with related phosphorus ylides in dichloromethane under mild conditions. These compound have been characterized by, elemental analysis and spectroscopic methods. The structure of complex 1 has been characterized crystallographically. This structure consists of five-membered ring formed by coordination of the ligand through the phosphine group and the ylidic carbon atom to the metal center. The coordination geometry around the Pd atoms in this complex can be defined as slightly distorted square planar. At a supramolecular level C -H center dot center dot center dot Cl and C-H center dot center dot center dot pi intermolecular interactions are responsible for the crystal packing. This complex has been found to act as efficient catalysts for the Suzuki cross-coupling reaction. Various aryl bromides were coupled with aryl boronic acids in DMF, under air, in the presence of 0.2 mol\% of the catalyst to afford corresponding cross- coupled products in good to excellent yields. (C) 2012 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; Panahimehr, Mohammad; Ahmadi, Mohsen, Bu Ali Sina Univ, Fac Chem, Hamadan 65174, Iran. Nasri, Zahra, Univ Isfahan, Dept Chem, Esfahan 8174673441, Iran. Khavasi, Hamid Reza, Shahid Beheshti Univ, Dept Chem, Tehran 1983963113, Iran.}}, author = {Sabounchei, Seyyed Javad and Panahimehr, Mohammad and Ahmadi, Mohsen and Nasri, Zahra and Khavasi, Hamid Reza}, author-email = {{jsabounchei@yahoo.co.uk}}, biburl = {https://www.bibsonomy.org/bibtex/2fbcd63787431b3ff3448f19c8fd98544/hkhavasi}, cited-references = {{Basu B, 2003, TETRAHEDRON LETT, V44, P3817, DOI 10.1016/S0040-4039(03)00731-7. Batchelor RJ, 1996, INORG CHEM, V35, P3667, DOI 10.1021/ic951151j. Bohm VPW, 2000, J ORGANOMET CHEM, V595, P186, DOI 10.1016/S0022-328X(99)00590-2. Chahen L, 2006, J ORGANOMET CHEM, V691, P4257, DOI 10.1016/j.jorganchem.2006.06.020. CHAMPNESS NR, 1995, INORG CHEM, V34, P651, DOI 10.1021/ic00107a019. Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO;2-N. Das P, 2010, TETRAHEDRON LETT, V51, P1479, DOI 10.1016/j.tetlet.2010.01.032. Diederich F, 2004, METAL CATALYZED CROS. 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USON R, 1987, J ORGANOMET CHEM, V334, P389, DOI 10.1016/0022-328X(87)80101-8. VICENTE J, 1991, J CHEM SOC DALTON, P2579, DOI 10.1039/dt9910002579. Wittig G., 1980, ANGEW CHEM, V92, P671, DOI 10.1002/ange.19800920904. Zhang CM, 2000, TETRAHEDRON LETT, V41, P595, DOI 10.1016/S0040-4039(99)02133-4. Zhang JL, 2006, J ORGANOMET CHEM, V691, P1301, DOI 10.1016/j.jorganchem.2005.11.027. Zhang ZH, 2006, J ORG CHEM, V71, P7485, DOI 10.1021/jo061179k.}}, doc-delivery-number = {{045FJ}}, doi = {{10.1016/j.jorganchem.2012.10.004}}, eissn = {{1872-8561}}, funding-acknowledgement = {{Bu-Ali Sina University}}, funding-text = {{We are grateful to the Bu-Ali Sina University for a grant and Mr. Zebarjadian for recording the NMR spectra. Our gratitude also goes to Miss. Behranj for all cooperation.}}, interhash = {8884f51bd166791a6dfbd726db296dea}, intrahash = {fbcd63787431b3ff3448f19c8fd98544}, issn = {{0022-328X}}, journal = {{JOURNAL OF ORGANOMETALLIC CHEMISTRY}}, journal-iso = {{J. Organomet. Chem.}}, keywords = {Crystal Suzuki catalyst; cross-coupling reaction} structure; {Palladium}, keywords-plus = {{CROSS-COUPLING REACTION; PLATINUM(II) HALIDE-COMPLEXES; PALLADIUM(II) COMPLEXES; STRUCTURAL-CHARACTERIZATION; ORGANOBORON COMPOUNDS; MERCURY(II) HALIDES; ORGANIC ELECTROPHILES; PHOSPHINE COMPLEXES; MOLECULAR-STRUCTURE; EFFICIENT CATALYST}}, language = {{English}}, month = {{JAN 1}}, number-of-cited-references = {{70}}, orcid-numbers = {{Ahmadi, Mohsen/0000-0002-7018-0460}}, pages = {{207-213}}, publisher = {{ELSEVIER SCIENCE SA}}, research-areas = {{Chemistry}}, researcherid-numbers = {{Ahmadi, Mohsen/A-6202-2012}}, times-cited = {{22}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Four-coordinate Pd(II) complexes containing non-symmetric phosphorus ylides: Synthesis, characterization, and catalytic behavior towards Suzuki reaction}}, type = {{Article}}, unique-id = {{ISI:000311680100030}}, usage-count-last-180-days = {{2}}, usage-count-since-2013 = {{35}}, volume = {{723}}, web-of-science-categories = {{Chemistry, Inorganic \& Nuclear; Chemistry, Organic}}, year = {{2013}} }