Article,
New dimeric phosphine ylide copper (I) complexes: Synthesis, coordination behavior, and application in Suzuki cross-coupling reactions
S. Sabounchei, M. Pourshahbaz, M. Ahmadi, A. Hashemi, and H. Khavasi.INORGANIC CHEMISTRY COMMUNICATIONS, (October 2013)
DOI: {10.1016/j.inoche.2013.08.010}
Abstract
The reaction of the non-symmetric phosphorus ylides,
Ph2P(CH2)(n)PPh2C(H)C(O)PhR with CuCl in equimolar ratios using dry
methanol as solvent give binuclear complexes of the type
Cu(mu-Cl)\Ph2P(CH2)(n)PPh2C(H)C(O)PhR\(2) (n = 1: R = Br (1), OCH3
(2); n = 2: R = Br (3), OCH3 (4)). X-ray analyses of 1 demonstrate the
Cl bridged dimeric structures with P,C-chelated ligands.
Characterizations of these compounds were carried out by FT-IR and
multinuclear NMR technique. Elemental analysis indicate a 1:1
stoichiometry between the ylides and the Cu(I) chloride in the four
complexes. The precursor complexes 1 and 3 are found to exhibit high
catalytic activity in the Cu-catalyzed Suzuki cross-coupling reactions
in an air atmosphere at medium catalyst loading in DMF as a solvent. The
use of 5 mol\% catalyst in the presence of Cs2CO3 allows the coupling
reaction to proceed with moderate to excellent yields. (C) 2013 Elsevier
B.V. All rights reserved.
- BibTeX key
- ISI:000327563700011
- entry type
- article
- address
- PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS
- year
- 2013
- month
- OCT
- journal
- INORGANIC CHEMISTRY COMMUNICATIONS
- pages
- 39-44
- publisher
- ELSEVIER SCIENCE BV
- volume
- 36
- type
- Article
- author-email
- jsabounchei@yahoo.co.uk
- research-areas
- Chemistry
- language
- English
- eissn
- 1879-0259
- funding-text
- We are grateful to the Bu-Ali Sina University for a grant and Mr. Zebarjadian for recording the NMR spectra.
- researcherid-numbers
- Ahmadi, Dr. Mohsen/A-6202-2012
- funding-acknowledgement
- Bu-Ali Sina University
- times-cited
- 2
- cited-references
- Anderson KW, 2005, ANGEW CHEM INT EDIT, V44, P6173, DOI 10.1002/anie.200502017. Barder TE, 2005, J AM CHEM SOC, V127, P4685, DOI 10.1021/ja042491j. Beletskaya IP, 2004, COORDIN CHEM REV, V248, P2337, DOI 10.1016/j.ccr.2004.09.014. Bokach NA, 2003, INORG CHEM, V42, P3602, DOI 10.1021/ic034086j. 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. Christau H. J., 1994, CHEM REV, V94, P1299. Diederich F., 2004, METAL CATALYZED CROS. Demir AS, 2003, J ORG CHEM, V68, P10130, DOI 10.1021/jo034680a. Ebrahim MM, 2007, POLYHEDRON, V26, P3491, DOI 10.1016/j.poly.2007.03.059. Ebrahim MM, 2009, J ORGANOMET CHEM, V694, P643, DOI 10.1016/j.jorganchem.2008.11.051. Facchin G., 1987, J CHEM SOC DA, V6, P1381. Falvello LR, 2003, INORG CHIM ACTA, V347, P75, DOI 10.1016/S0020-1693(02)01448-2. Falvello LR, 2000, INORG CHEM, V39, P2957, DOI 10.1021/ic990923z. Gu SJ, 2012, INORG CHEM COMMUN, V21, P168, DOI 10.1016/j.inoche.2012.05.007. Gujadhur R, 2001, TETRAHEDRON LETT, V42, P4791, DOI 10.1016/S0040-4039(01)00888-7. Hassan J, 2002, CHEM REV, V102, P1359, DOI 10.1021/cr000664r. Hassan J., 2007, ACCOUNTS CHEM RES, V40, P676. Hatakeyama T, 2010, J AM CHEM SOC, V132, P10674, DOI 10.1021/ja103973a. Heinicke J, 2005, J ORGANOMET CHEM, V690, P2449, DOI 10.1016/j.jorganchem.2004.10.012. Hierso JC, 2005, TETRAHEDRON, V61, P9759, DOI 10.1016/j.tet.2005.06.065. HOLY NL, 1976, J AM CHEM SOC, V98, P7823, DOI 10.1021/ja00440a062. Janardanan D, 2007, CHEM-EUR J, V13, P4805, DOI 10.1002/chem.200700303. Karami K, 2011, J ORGANOMET CHEM, V696, P940, DOI 10.1016/j.jorganchem.2010.10.025. Karimi B, 2011, INORG CHEM, V50, P6063, DOI 10.1021/ic2000766. Kokotos CG, 2007, ORG LETT, V9, P2099, DOI 10.1021/ol070507f. Kolodiazhnyi OI, 1996, TETRAHEDRON, V52, P1855, DOI 10.1016/0040-4020(95)00433-5. Ley SV, 2003, ANGEW CHEM INT EDIT, V42, P5400, DOI 10.1002/anie.200300594. Li JH, 2007, J ORG CHEM, V72, P2053, DOI 10.1021/jo0623742. Li JH, 2006, EUR J ORG CHEM, P2063, DOI 10.1002/ejoc.200600026. Liang LC, 2005, ORGANOMETALLICS, V24, P353, DOI 10.1021/om0492395. LIN IJB, 1990, J CHEM SOC DALTON, P2509, DOI 10.1039/dt9900002509. Littke AF, 1998, ANGEW CHEM INT EDIT, V37, P3387. Liu JD, 2012, TETRAHEDRON LETT, V53, P5678, DOI 10.1016/j.tetlet.2012.08.044. Mao JC, 2008, TETRAHEDRON, V64, P3905, DOI 10.1016/j.tet.2008.02.068. MIYAURA N, 1995, CHEM REV, V95, P2457, DOI 10.1021/cr00039a007. Miyaura N., 2002, CROSS COUPLING REACT. Molander GA, 2002, ORG LETT, V4, P107, DOI 10.1021/ol0169729. Nonnenmacher M, 2007, J ORGANOMET CHEM, V692, P2554, DOI 10.1016/j.jorganchem.2007.02.044. OOSAWA Y, 1976, J ORGANOMET CHEM, V122, P113, DOI 10.1016/S0022-328X(00)92752-9. Percec V, 2004, J ORG CHEM, V69, P3447, DOI 10.1021/jo049940i. Punji B, 2007, INORG CHEM, V46, P10268, DOI 10.1021/ic701537k. Rodriguez CJ, 2004, CHEM COMMUN, P1720, DOI 10.1039/b404783d. Sabounchei SJ, 2008, J ORGANOMET CHEM, V693, P1975, DOI 10.1016/j.jorganchem.2008.02.025. Sabounchei SJ, 2007, J ORGANOMET CHEM, V692, P2500, DOI 10.1016/j.jorganchem.2007.02.027. Sabounchei SJ, 2013, INORG CHIM ACTA, V405, P15, DOI 10.1016/j.ica.2013.04.048. Sabounchei SJ, 2013, CATAL COMMUN, V37, P114, DOI 10.1016/j.catcom.2013.03.028. Sabounchei SJ, 2013, J COORD CHEM, V66, P411, DOI 10.1080/00958972.2012.759216. Sabounchei SJ, 2013, J ORGANOMET CHEM, V723, P207, DOI 10.1016/j.jorganchem.2012.10.004. Sabounchei SJ, 2010, INORG CHIM ACTA, V363, P3973, DOI 10.1016/j.ica.2010.07.072. Sabounchei SJ, 2010, INORG CHIM ACTA, V363, P3654, DOI 10.1016/j.ica.2010.05.004. Sabounchei SJ, 2010, J ORGANOMET CHEM, V695, P1441, DOI 10.1016/j.jorganchem.2010.02.029. Sabounchei SJ, 2009, INORG CHIM ACTA, V362, P105, DOI 10.1016/j.ica.2008.03.015. Saravanabharathi D, 2003, P INDIAN AS-CHEM SCI, V115, P741. Sbovata SM, 2008, INORG CHIM ACTA, V361, P3177, DOI 10.1016/j.ica.2007.10.055. Seth DK, 2011, POLYHEDRON, V30, P2438, DOI 10.1016/j.poly.2011.05.037. Siemsen P, 2000, ANGEW CHEM INT EDIT, V39, P2632, DOI 10.1002/1521-3773(20000804)39:152632:AID-ANIE26323.0. CO, DOI 10.1002/1521-3773(20000804)39:15<2632::AID-ANIE2632>3.0.CO;2-F. SLATER JC, 1964, J CHEM PHYS, V41, P3199, DOI 10.1063/1.1725697. Spannenberg A, 2000, ORGANOMETALLICS, V19, P3991, DOI 10.1021/om000429z. TAKAHASHI H, 1976, CHEM LETT, P15, DOI 10.1246/cl.1976.15. TAKAHASHI H, 1977, B CHEM SOC JPN, V50, P1771, DOI 10.1246/bcsj.50.1771. TEAGLE JA, 1986, INORG CHIM ACTA, V118, P65, DOI 10.1016/S0020-1693(00)86408-7. Thathagar MB, 2003, ADV SYNTH CATAL, V345, P979, DOI 10.1002/adsc.200303045. Thathagar MB, 2002, J AM CHEM SOC, V124, P11858, DOI 10.1021/ja027716+. Tobisu M, 2011, J AM CHEM SOC, V133, P19505, DOI 10.1021/ja207759e. 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. Wagner G, 2001, INORG CHEM, V40, P1683, DOI 10.1021/ic000769c. Wolfe JP, 1999, J AM CHEM SOC, V121, P9550, DOI 10.1021/ja992130h. Wolfe JP, 2000, J ORG CHEM, V65, P1158, DOI 10.1021/jo991699y. YAMAMOTO Y, 1975, J ORGANOMET CHEM, V96, P133, DOI 10.1016/S0022-328X(00)86429-3. Yang HQ, 2010, GREEN CHEM, V12, P441, DOI 10.1039/b919175e. Zapf A, 2000, CHEM-EUR J, V6, P1830, DOI 10.1002/(SICI)1521-3765(20000515)6:10<1830::AID-CHEM1830>3.3.CO;2-\#. Zhou J, 2009, J ORGANOMET CHEM, V694, P697, DOI 10.1016/j.jorganchem.2008.11.060. Zim D, 2001, ORG LETT, V3, P3049, DOI 10.1021/ol016526l.
- issn
- 1387-7003
- affiliation
- Sabounchei, SJ (Reprint Author), Bu Ali Sina Univ, Fac Chem, Hamadan 65174, Iran. Sabounchei, Seyyed Javad; Pourshahbaz, Mahbubeh; Ahmadi, Mohsen; Hashemi, Ali, Bu Ali Sina Univ, Fac Chem, Hamadan 65174, Iran. Khavasi, Hamid Reza, Shahid Beheshti Univ, Dept Chem, GC, Tehran 1983963113, Iran.
- orcid-numbers
- Ahmadi, Dr. Mohsen/0000-0002-7018-0460
- usage-count-since-2013
- 11
- doc-delivery-number
- 259ZB
- web-of-science-categories
- Chemistry, Inorganic & Nuclear
- usage-count-last-180-days
- 0
- number-of-cited-references
- 74
- journal-iso
- Inorg. Chem. Commun.
- keywords-plus
- STABILIZED PHOSPHORUS YLIDES; BINUCLEAR MERCURY(II) COMPLEXES; STRUCTURAL-CHARACTERIZATION; ARYLBORONIC ACIDS; ARYL CHLORIDES; PALLADIUM(II) COMPLEXES; CRYSTAL-STRUCTURE; CATALYTIC-PROPERTIES; MOLECULAR-STRUCTURE; HALIDE-COMPLEXES
- unique-id
- ISI:000327563700011
- DOI
- 10.1016/j.inoche.2013.08.010
Tags
- activity;
- catalytic
- complex;
- copper-catalyzed}
- cross-coupling
- crystal
- cu(i)
- high
- reaction;
- structure;
- suzuki
- x-ray
- ylide;
- {phosphorus
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%1 ISI:000327563700011
%A Sabounchei, Seyyed Javad
%A Pourshahbaz, Mahbubeh
%A Ahmadi, Mohsen
%A Hashemi, Ali
%A Khavasi, Hamid Reza
%C PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS
%D 2013
%I ELSEVIER SCIENCE BV
%J INORGANIC CHEMISTRY COMMUNICATIONS
%K Copper-catalyzed} Cu(I) High Suzuki X-ray activity; catalytic complex; cross-coupling crystal reaction; structure; ylide; {Phosphorus
%P 39-44
%R 10.1016/j.inoche.2013.08.010
%T New dimeric phosphine ylide copper (I) complexes: Synthesis,
coordination behavior, and application in Suzuki cross-coupling
reactions
%V 36
%X The reaction of the non-symmetric phosphorus ylides,
Ph2P(CH2)(n)PPh2C(H)C(O)PhR with CuCl in equimolar ratios using dry
methanol as solvent give binuclear complexes of the type
Cu(mu-Cl)\Ph2P(CH2)(n)PPh2C(H)C(O)PhR\(2) (n = 1: R = Br (1), OCH3
(2); n = 2: R = Br (3), OCH3 (4)). X-ray analyses of 1 demonstrate the
Cl bridged dimeric structures with P,C-chelated ligands.
Characterizations of these compounds were carried out by FT-IR and
multinuclear NMR technique. Elemental analysis indicate a 1:1
stoichiometry between the ylides and the Cu(I) chloride in the four
complexes. The precursor complexes 1 and 3 are found to exhibit high
catalytic activity in the Cu-catalyzed Suzuki cross-coupling reactions
in an air atmosphere at medium catalyst loading in DMF as a solvent. The
use of 5 mol\% catalyst in the presence of Cs2CO3 allows the coupling
reaction to proceed with moderate to excellent yields. (C) 2013 Elsevier
B.V. All rights reserved.
@article{ISI:000327563700011,
abstract = {{The reaction of the non-symmetric phosphorus ylides,
Ph2P(CH2)(n)PPh2C(H)C(O)PhR with CuCl in equimolar ratios using dry
methanol as solvent give binuclear complexes of the type
{[}Cu(mu-Cl)\{Ph2P(CH2)(n)PPh2C(H)C(O)PhR\}](2) (n = 1: R = Br (1), OCH3
(2); n = 2: R = Br (3), OCH3 (4)). X-ray analyses of 1 demonstrate the
Cl bridged dimeric structures with P,C-chelated ligands.
Characterizations of these compounds were carried out by FT-IR and
multinuclear NMR technique. Elemental analysis indicate a 1:1
stoichiometry between the ylides and the Cu(I) chloride in the four
complexes. The precursor complexes 1 and 3 are found to exhibit high
catalytic activity in the Cu-catalyzed Suzuki cross-coupling reactions
in an air atmosphere at medium catalyst loading in DMF as a solvent. The
use of 5 mol\% catalyst in the presence of Cs2CO3 allows the coupling
reaction to proceed with moderate to excellent yields. (C) 2013 Elsevier
B.V. All rights reserved.}},
added-at = {2017-05-10T15:29:29.000+0200},
address = {{PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS}},
affiliation = {{Sabounchei, SJ (Reprint Author), Bu Ali Sina Univ, Fac Chem, Hamadan 65174, Iran.
Sabounchei, Seyyed Javad; Pourshahbaz, Mahbubeh; Ahmadi, Mohsen; Hashemi, Ali, Bu Ali Sina Univ, Fac Chem, Hamadan 65174, Iran.
Khavasi, Hamid Reza, Shahid Beheshti Univ, Dept Chem, GC, Tehran 1983963113, Iran.}},
author = {Sabounchei, Seyyed Javad and Pourshahbaz, Mahbubeh and Ahmadi, Mohsen and Hashemi, Ali and Khavasi, Hamid Reza},
author-email = {{jsabounchei@yahoo.co.uk}},
biburl = {https://www.bibsonomy.org/bibtex/2297e31e42e82a2dc3550f5230dfc7b0f/hkhavasi},
cited-references = {{Anderson KW, 2005, ANGEW CHEM INT EDIT, V44, P6173, DOI 10.1002/anie.200502017.
Barder TE, 2005, J AM CHEM SOC, V127, P4685, DOI 10.1021/ja042491j.
Beletskaya IP, 2004, COORDIN CHEM REV, V248, P2337, DOI 10.1016/j.ccr.2004.09.014.
Bokach NA, 2003, INORG CHEM, V42, P3602, DOI 10.1021/ic034086j.
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.
Christau H. J., 1994, CHEM REV, V94, P1299.
Diederich F., 2004, METAL CATALYZED CROS.
Demir AS, 2003, J ORG CHEM, V68, P10130, DOI 10.1021/jo034680a.
Ebrahim MM, 2007, POLYHEDRON, V26, P3491, DOI 10.1016/j.poly.2007.03.059.
Ebrahim MM, 2009, J ORGANOMET CHEM, V694, P643, DOI 10.1016/j.jorganchem.2008.11.051.
Facchin G., 1987, J CHEM SOC DA, V6, P1381.
Falvello LR, 2003, INORG CHIM ACTA, V347, P75, DOI 10.1016/S0020-1693(02)01448-2.
Falvello LR, 2000, INORG CHEM, V39, P2957, DOI 10.1021/ic990923z.
Gu SJ, 2012, INORG CHEM COMMUN, V21, P168, DOI 10.1016/j.inoche.2012.05.007.
Gujadhur R, 2001, TETRAHEDRON LETT, V42, P4791, DOI 10.1016/S0040-4039(01)00888-7.
Hassan J, 2002, CHEM REV, V102, P1359, DOI 10.1021/cr000664r.
Hassan J., 2007, ACCOUNTS CHEM RES, V40, P676.
Hatakeyama T, 2010, J AM CHEM SOC, V132, P10674, DOI 10.1021/ja103973a.
Heinicke J, 2005, J ORGANOMET CHEM, V690, P2449, DOI 10.1016/j.jorganchem.2004.10.012.
Hierso JC, 2005, TETRAHEDRON, V61, P9759, DOI 10.1016/j.tet.2005.06.065.
HOLY NL, 1976, J AM CHEM SOC, V98, P7823, DOI 10.1021/ja00440a062.
Janardanan D, 2007, CHEM-EUR J, V13, P4805, DOI 10.1002/chem.200700303.
Karami K, 2011, J ORGANOMET CHEM, V696, P940, DOI 10.1016/j.jorganchem.2010.10.025.
Karimi B, 2011, INORG CHEM, V50, P6063, DOI 10.1021/ic2000766.
Kokotos CG, 2007, ORG LETT, V9, P2099, DOI 10.1021/ol070507f.
Kolodiazhnyi OI, 1996, TETRAHEDRON, V52, P1855, DOI 10.1016/0040-4020(95)00433-5.
Ley SV, 2003, ANGEW CHEM INT EDIT, V42, P5400, DOI 10.1002/anie.200300594.
Li JH, 2007, J ORG CHEM, V72, P2053, DOI 10.1021/jo0623742.
Li JH, 2006, EUR J ORG CHEM, P2063, DOI 10.1002/ejoc.200600026.
Liang LC, 2005, ORGANOMETALLICS, V24, P353, DOI 10.1021/om0492395.
LIN IJB, 1990, J CHEM SOC DALTON, P2509, DOI 10.1039/dt9900002509.
Littke AF, 1998, ANGEW CHEM INT EDIT, V37, P3387.
Liu JD, 2012, TETRAHEDRON LETT, V53, P5678, DOI 10.1016/j.tetlet.2012.08.044.
Mao JC, 2008, TETRAHEDRON, V64, P3905, DOI 10.1016/j.tet.2008.02.068.
MIYAURA N, 1995, CHEM REV, V95, P2457, DOI 10.1021/cr00039a007.
Miyaura N., 2002, CROSS COUPLING REACT.
Molander GA, 2002, ORG LETT, V4, P107, DOI 10.1021/ol0169729.
Nonnenmacher M, 2007, J ORGANOMET CHEM, V692, P2554, DOI 10.1016/j.jorganchem.2007.02.044.
OOSAWA Y, 1976, J ORGANOMET CHEM, V122, P113, DOI 10.1016/S0022-328X(00)92752-9.
Percec V, 2004, J ORG CHEM, V69, P3447, DOI 10.1021/jo049940i.
Punji B, 2007, INORG CHEM, V46, P10268, DOI 10.1021/ic701537k.
Rodriguez CJ, 2004, CHEM COMMUN, P1720, DOI 10.1039/b404783d.
Sabounchei SJ, 2008, J ORGANOMET CHEM, V693, P1975, DOI 10.1016/j.jorganchem.2008.02.025.
Sabounchei SJ, 2007, J ORGANOMET CHEM, V692, P2500, DOI 10.1016/j.jorganchem.2007.02.027.
Sabounchei SJ, 2013, INORG CHIM ACTA, V405, P15, DOI 10.1016/j.ica.2013.04.048.
Sabounchei SJ, 2013, CATAL COMMUN, V37, P114, DOI 10.1016/j.catcom.2013.03.028.
Sabounchei SJ, 2013, J COORD CHEM, V66, P411, DOI 10.1080/00958972.2012.759216.
Sabounchei SJ, 2013, J ORGANOMET CHEM, V723, P207, DOI 10.1016/j.jorganchem.2012.10.004.
Sabounchei SJ, 2010, INORG CHIM ACTA, V363, P3973, DOI 10.1016/j.ica.2010.07.072.
Sabounchei SJ, 2010, INORG CHIM ACTA, V363, P3654, DOI 10.1016/j.ica.2010.05.004.
Sabounchei SJ, 2010, J ORGANOMET CHEM, V695, P1441, DOI 10.1016/j.jorganchem.2010.02.029.
Sabounchei SJ, 2009, INORG CHIM ACTA, V362, P105, DOI 10.1016/j.ica.2008.03.015.
Saravanabharathi D, 2003, P INDIAN AS-CHEM SCI, V115, P741.
Sbovata SM, 2008, INORG CHIM ACTA, V361, P3177, DOI 10.1016/j.ica.2007.10.055.
Seth DK, 2011, POLYHEDRON, V30, P2438, DOI 10.1016/j.poly.2011.05.037.
Siemsen P, 2000, ANGEW CHEM INT EDIT, V39, P2632, DOI {[}10.1002/1521-3773(20000804)39:152632:AID-ANIE26323.0. CO, DOI 10.1002/1521-3773(20000804)39:15<2632::AID-ANIE2632>3.0.CO;2-F].
SLATER JC, 1964, J CHEM PHYS, V41, P3199, DOI 10.1063/1.1725697.
Spannenberg A, 2000, ORGANOMETALLICS, V19, P3991, DOI 10.1021/om000429z.
TAKAHASHI H, 1976, CHEM LETT, P15, DOI 10.1246/cl.1976.15.
TAKAHASHI H, 1977, B CHEM SOC JPN, V50, P1771, DOI 10.1246/bcsj.50.1771.
TEAGLE JA, 1986, INORG CHIM ACTA, V118, P65, DOI 10.1016/S0020-1693(00)86408-7.
Thathagar MB, 2003, ADV SYNTH CATAL, V345, P979, DOI 10.1002/adsc.200303045.
Thathagar MB, 2002, J AM CHEM SOC, V124, P11858, DOI 10.1021/ja027716+.
Tobisu M, 2011, J AM CHEM SOC, V133, P19505, DOI 10.1021/ja207759e.
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.
Wagner G, 2001, INORG CHEM, V40, P1683, DOI 10.1021/ic000769c.
Wolfe JP, 1999, J AM CHEM SOC, V121, P9550, DOI 10.1021/ja992130h.
Wolfe JP, 2000, J ORG CHEM, V65, P1158, DOI 10.1021/jo991699y.
YAMAMOTO Y, 1975, J ORGANOMET CHEM, V96, P133, DOI 10.1016/S0022-328X(00)86429-3.
Yang HQ, 2010, GREEN CHEM, V12, P441, DOI 10.1039/b919175e.
Zapf A, 2000, CHEM-EUR J, V6, P1830, DOI 10.1002/(SICI)1521-3765(20000515)6:10<1830::AID-CHEM1830>3.3.CO;2-\#.
Zhou J, 2009, J ORGANOMET CHEM, V694, P697, DOI 10.1016/j.jorganchem.2008.11.060.
Zim D, 2001, ORG LETT, V3, P3049, DOI 10.1021/ol016526l.}},
doc-delivery-number = {{259ZB}},
doi = {{10.1016/j.inoche.2013.08.010}},
eissn = {{1879-0259}},
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.}},
interhash = {2c67d89d6b4fb3747760bc9a0d7e1aea},
intrahash = {297e31e42e82a2dc3550f5230dfc7b0f},
issn = {{1387-7003}},
journal = {{INORGANIC CHEMISTRY COMMUNICATIONS}},
journal-iso = {{Inorg. Chem. Commun.}},
keywords = {Copper-catalyzed} Cu(I) High Suzuki X-ray activity; catalytic complex; cross-coupling crystal reaction; structure; ylide; {Phosphorus},
keywords-plus = {{STABILIZED PHOSPHORUS YLIDES; BINUCLEAR MERCURY(II) COMPLEXES;
STRUCTURAL-CHARACTERIZATION; ARYLBORONIC ACIDS; ARYL CHLORIDES;
PALLADIUM(II) COMPLEXES; CRYSTAL-STRUCTURE; CATALYTIC-PROPERTIES;
MOLECULAR-STRUCTURE; HALIDE-COMPLEXES}},
language = {{English}},
month = {{OCT}},
number-of-cited-references = {{74}},
orcid-numbers = {{Ahmadi, Dr. Mohsen/0000-0002-7018-0460}},
pages = {{39-44}},
publisher = {{ELSEVIER SCIENCE BV}},
research-areas = {{Chemistry}},
researcherid-numbers = {{Ahmadi, Dr. Mohsen/A-6202-2012}},
times-cited = {{2}},
timestamp = {2017-05-10T15:29:29.000+0200},
title = {{New dimeric phosphine ylide copper (I) complexes: Synthesis,
coordination behavior, and application in Suzuki cross-coupling
reactions}},
type = {{Article}},
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volume = {{36}},
web-of-science-categories = {{Chemistry, Inorganic \& Nuclear}},
year = {{2013}}
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