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Journal articles on the topic 'Bisphosphines'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Jones, Nathan D., Patric Meessen, Martin B. Smith, Udo Losehand, Steven J. Rettig, Brian O. Patrick, and Brian R. James. "Bisphosphine ligands containing two o-N,N-dimethylanilinyl substituents at each phosphorus atom." Canadian Journal of Chemistry 80, no. 11 (November 1, 2002): 1600–1606. http://dx.doi.org/10.1139/v02-127.

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The synthesis and complete characterization of the family of tetra(amine)bisphosphine ligands (o-NMe2C6H4)2P-(X)-P(o-NMe2C6H4)2, where X = CH2 (dmapm), (CH2)2 (dmape), and [Formula: see text] (dmapcp), are described. Crystal structure data are compared with known, analogous bisphosphines containing o-pyridyl or phenyl substituents in place of the o-dimethylanilinyl groups. Several short, intramolecular C-H···N distances in the anilinyl derivatives may represent the presence of weak hydrogen bonds. Key words: phosphine, amine, polydentate, hydrogen-bonding to N atoms.

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2

Förstera, Daniela, Ingo Hartenbach, Martin Nieger, and Dietrich Gudat. "On the Synthesis and Addition Reactions of Chiral N-Heterocyclic Diphosphines." Zeitschrift für Naturforschung B 67, no. 8 (August 1, 2012): 765–73. http://dx.doi.org/10.5560/znb.2012-0177.

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Reaction of chiral N-heterocyclic chlorophosphines with lithium diphenylphosphide or of achiral N-heterocyclic chlorophosphines with optically active lithium menthyl phosphide produces chiral N-heterocyclic diphosphines which can be utilized in subsequent diphosphination reactions with activated alkenes or alkynes. The reaction with alkynes proceeds stereospecifically to produce Zethylene- 1,2-bisphosphines which are readily converted to nickel(II) or palladium(II) complexes. Reactions with alkenes are synthetically less useful as the addition proceeds without any chiral induction at the newly formed stereocenters to yield inseparable mixtures of diastereomeric products. The molecular structures of chiral Z-ethylene-1,2-bisphosphine complexes and of a chiral N-heterocyclic chlorophosphine have been determined by single-crystal X-ray diffraction

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3

Allen, Aberdeen, Ling Ma, and Wenbin Lin. "Facile synthesis of chelating bisphosphine oxides and bisphosphines via palladium-catalyzed bishydrophosphinylation reactions." Tetrahedron Letters 43, no. 20 (May 2002): 3707–10. http://dx.doi.org/10.1016/s0040-4039(02)00609-3.

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4

Allen Jr., Aberdeen, Ling Ma, and Wenbin Lin. "ChemInform Abstract: Facile Synthesis of Chelating Bisphosphine Oxides and Bisphosphines via Palladium-Catalyzed Bishydrophosphinylation Reactions." ChemInform 33, no. 36 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200236169.

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5

Gourdel, Yann, Pascal Pellon, Loïc Toupet, and Maurice Le Corre. "Stereoselective synthesis of new functionalized bisphosphines." Tetrahedron Letters 35, no. 8 (February 1994): 1197–200. http://dx.doi.org/10.1016/0040-4039(94)88022-0.

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6

Bhat, Sajad A., Joel T. Mague, and Maravanji S. Balakrishna. "Gold(i) complexes of bisphosphines with bis(azol-1-yl)methane backbone: structure of a rare dinuclear gold(i) complex [(Au2Cl){CH2(1,2-C3H2N2PPh2)2}3Cl]." Dalton Transactions 44, no. 40 (2015): 17696–703. http://dx.doi.org/10.1039/c5dt03161c.

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7

Fourmigue, Marc, Sylvia Jarshow, and Patrick Batail. "New Tertiary Phosphines and Bisphosphines-Functionalized Tetrathiafulvalenes." Phosphorus, Sulfur, and Silicon and the Related Elements 75, no. 1-4 (February 1993): 175–84. http://dx.doi.org/10.1080/10426509308037393.

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8

Genet, Cédric, Steven J. Canipa, Peter O'Brien, and Sven Taylor. "Catalytic Asymmetric Synthesis of Ferrocenes andP-Stereogenic Bisphosphines." Journal of the American Chemical Society 128, no. 29 (July 2006): 9336–37. http://dx.doi.org/10.1021/ja062616f.

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9

GOURDEL, Y., P. PELLON, L. TOUPET, and M. LE CORRE. "ChemInform Abstract: Stereoselective Synthesis of New Functionalized Bisphosphines." ChemInform 25, no. 28 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199428231.

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10

Bhat, Sajad A., Madhusudan K. Pandey, Joel T. Mague, and Maravanji S. Balakrishna. "Coordination of bis(azol-1-yl)methane-based bisphosphines towards RuII, RhI, PdII and PtII: synthesis, structural and catalytic studies." Dalton Transactions 46, no. 1 (2017): 227–41. http://dx.doi.org/10.1039/c6dt04094b.

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This paper describes the transition metal chemistry of three bis(X-diphenylphosphino-azol-1-yl)-based bisphosphines: bis(2-Ph₂P-imidazol-1-yl)methane (1), bis(5-Ph₂P-pyrazol-1-yl)methane (2) and bis(5-Ph₂P-1,2,4-triazol-1-yl)methane (3). These show versatility in their coordination behaviour.

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11

Zhang, Song-Lin, and Wen-Feng Bie. "Ligand-dependent formation of ion-pair CuI/CuIII trifluoromethyl complexes containing bisphosphines." Dalton Transactions 45, no. 44 (2016): 17588–92. http://dx.doi.org/10.1039/c6dt03016e.

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Novel ion-pair Cu^I/Cu^III trifluoromethyl complexes with representative bisphosphines are isolated and fully characterized to feature square planar [Cu^III(CF₃)₄]⁻ and tetrahedral [L₂Cu]⁺ units. They show unprecedented excellent reactivity for aerobic trifluoromethylation of arylboronic acids in generally good to quantitative yields.

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12

Nagaoka, Yasuo, Hideki Inoue, Nawal El-Koussi, and Kiyoshi Tomioka. "Synthesis and application of chiral bisphosphines through lithiation–conjugate addition tandem cyclization of chiral α,β,ψ,ω-unsaturated bisphosphine oxide." Chemical Communications, no. 2 (January 7, 2002): 122–23. http://dx.doi.org/10.1039/b109269c.

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13

McKinstry, Lydia, and Tom Livinghouse. "An efficient procedure for the synthesis of C-chiral bisphosphines." Tetrahedron 51, no. 28 (July 1995): 7655–66. http://dx.doi.org/10.1016/0040-4020(95)00390-t.

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14

Burck, Sebastian, Imre Hajdók, Martin Nieger, Denis Bubrin, Simon Schulze, Dietrich Gudat, and Dietrich Gudat. "Activation of Polarized Phosphorus–Phosphorus Bonds by Alkynes: Rational Synthesis of Unsymmetrical 1,2-Bisphosphine Ligands and Their Complexes." Zeitschrift für Naturforschung B 64, no. 1 (January 1, 2009): 63–72. http://dx.doi.org/10.1515/znb-2009-0109.

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The reactions of 1,1-diamino-2,2-diphenyl-substituted diphosphines featuring various degrees of P-P bond polarization with different alkynes were investigated. All diphosphines reacted with alkynes carrying one or two electron withdrawing carboxylic ester moieties under cleavage of the P-P bond and stereospecific phosphinyl-phosphination at the triple bond to give unsymmetrical ethane-1,2- bisphosphines. Several of the products were further converted into chelate complexes upon reaction with group-10 metal dihalides. All isolated compounds were characterized by analytical and spectroscopic data, and several of the new ligands and complexes by single-crystal X-ray diffraction studies.

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15

Falk, Florian C., Peter Oechsle, Werner R. Thiel, Constantin-Gabriel Daniliuc, and Jan Paradies. "Unsymmetrical Bisphosphines for the Amidation of Aryl Chlorides: A Kinetic Study." European Journal of Organic Chemistry 2014, no. 17 (May 2, 2014): 3637–45. http://dx.doi.org/10.1002/ejoc.201400159.

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16

MCKINSTRY, L., and T. LIVINGHOUSE. "ChemInform Abstract: Efficient Procedure for the Synthesis of C-Chiral Bisphosphines." ChemInform 26, no. 45 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199545206.

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17

Jiao, Yunzhe, Marta Serrano Torne, Jose Gracia, J. W. (Hans) Niemantsverdriet, and Piet W. N. M. van Leeuwen. "Ligand effects in rhodium-catalyzed hydroformylation with bisphosphines: steric or electronic?" Catalysis Science & Technology 7, no. 6 (2017): 1404–14. http://dx.doi.org/10.1039/c6cy01990k.

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18

Li, Chunbao, Bruno Bernet, Andrea Vasella, Emil A. Broger, and Arthur Meili. "Synthesis and evaluation in asymmetric hydrogenation of carbohydrate-derived 1,3-bisphosphines." Carbohydrate Research 216 (September 1992): 149–69. http://dx.doi.org/10.1016/0008-6215(92)84158-o.

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19

Nagaoka, Yasuo, Hideki Inoue, Nawal El-Koussi, and Kiyoshi Tomioka. "ChemInform Abstract: Synthesis and Application of Chiral Bisphosphines Through Lithiation-Conjugate Addition Tandem Cyclization of Chiral α,β,ψ,ω-Unsaturated Bisphosphine Oxide." ChemInform 33, no. 19 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200219032.

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20

Genet, Jean Pierre. "Recent studies on asymmetric hydrogenation. New catalysts and synthetic applications in organic synthesis." Pure and Applied Chemistry 74, no. 1 (January 1, 2002): 77–83. http://dx.doi.org/10.1351/pac200274010077.

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CODRu(h3methylallyl)2 is a versatile starting material for the preparation of a wide range of chiral bisphosphines ruthenium(II) complexes: (P*P)Ru(h3methylallyl)2 2, Ru[X4(P*P)2] 3, and cationic monohydride ruthenium complex 4. A facile synthesis of new C2 electron-rich chiral phosphines, bis(phosphetano)benzene 8 and 1,1¢bis(phosphetano)ferrocene 10 is presented. Dynamic kinetic resolution was used for efficient syntheses of key components of the hexahydroazepane core 16 of balanol and of optically pure Boc-(2S,3R,3S)-iso-dolaproïne 19. Catalyst 4 was used in asymmetric hydrogenation of 22 to give (+)-cis-methyl dihydrojasmonate in high enantioselectivity.

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21

Morisaki, Y., K. Saito, H. Imoto, K. Suzuki, Y. Ouchi, and Y. Chujo. "Synthesis of optically active polymers using P-chiral bisphosphines as anionic initiators." Polymer Science Series A 51, no. 11-12 (December 2009): 1218–28. http://dx.doi.org/10.1134/s0965545x09110066.

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22

Chisholm, Danielle M., Allen G. Oliver, and J. Scott McIndoe. "Mono-alkylated bisphosphines as dopants for ESI-MS analysis of catalytic reactions." Dalton Trans. 39, no. 2 (2010): 364–73. http://dx.doi.org/10.1039/b913225b.

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23

McKinstry, Lydia, and Tom Livinghouse. "An efficient procedure for the synthesis of electron rich bisphosphines containing homochiral backbones." Tetrahedron Letters 35, no. 50 (December 1994): 9319–22. http://dx.doi.org/10.1016/s0040-4039(00)78531-5.

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24

County, Geoffrey R., Ron S. Dickson, Gary D. Fallon, Susan M. Jenkins, and Julian Johnson. "Comparison of the reactions of some bisphosphines with two related dinuclear rhodium complexes." Journal of Organometallic Chemistry 526, no. 2 (December 1996): 279–93. http://dx.doi.org/10.1016/s0022-328x(96)06535-7.

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25

Braunschweig, Holger, Ralph Leech, Daniela Rais, Krzysztof Radacki, and Katharina Uttinger. "Conversion oftrans-Bromoboryl Platinum Complexes into theircis-Analogues upon Treatment with Chelating Bisphosphines." Organometallics 27, no. 3 (February 2008): 418–22. http://dx.doi.org/10.1021/om700976t.

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26

Shaw, Anthony P., Jack R. Norton, Daniela Buccella, Lauren A. Sites, Shannon S. Kleinbach, Daniel A. Jarem, Katherine M. Bocage, and Chip Nataro. "Synthesis, Electrochemistry, and Reactivity of Half-Sandwich Ruthenium Complexes Bearing Metallocene-Based Bisphosphines." Organometallics 28, no. 13 (July 13, 2009): 3804–14. http://dx.doi.org/10.1021/om900062a.

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27

Hayashi, Ryo, Kazuhiro Nakatsui, Daisuke Sugiyama, Toshiki Kitajima, Nobuhiko Oohara, Masashi Sugiya, Satoshi Osada, and Hiroaki Kodama. "Anti-tumor activities of Au(I) complexed with bisphosphines in HL-60 cells." Journal of Inorganic Biochemistry 137 (August 2014): 109–14. http://dx.doi.org/10.1016/j.jinorgbio.2014.04.006.

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28

LI, C., B. BERNET, A. VASELLA, E. A. BROGER, and A. MEILI. "ChemInform Abstract: Synthesis and Evaluation in Asymmetric Hydrogenation of Carbohydrate- Derived 1,3-Bisphosphines." ChemInform 23, no. 46 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199246054.

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29

Genov, Daniel G. "A NEW EFFICIENT PROTOCOL FOR THE PREPARATION OF CHIRAL BISPHOSPHINES OF THE BICP FAMILY." Phosphorus, Sulfur, and Silicon and the Related Elements 179, no. 10 (October 1, 2004): 1949–58. http://dx.doi.org/10.1080/10426500490466977.

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30

Morisaki, Y., K. Saito, H. Imoto, K. Suzuki, Y. Ouchi, and Y. Chujo. "Erratum to: “Synthesis of Optically Active Polymers Using P-Chiral Bisphosphines as Anionic Initiators”." Polymer Science Series A 52, no. 4 (April 2010): 462. http://dx.doi.org/10.1134/s0965545x10040176.

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31

Colebatch, Annie L., Alasdair I. McKay, Nicholas A. Beattie, Stuart A. Macgregor, and Andrew S. Weller. "Fluoroarene Complexes with Small Bite Angle Bisphosphines: Routes to Amine-Borane and Aminoborylene Complexes." European Journal of Inorganic Chemistry 2017, no. 38-39 (August 4, 2017): 4533–40. http://dx.doi.org/10.1002/ejic.201700600.

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32

Zhang, Yong Jian, Jung Hwan Park, and Sang-gi Lee. "Asymmetric synthesis of homoproline derivatives via Rh(I)-catalyzed hydrogenation using chiral bisphosphines as ligands." Tetrahedron: Asymmetry 15, no. 14 (July 2004): 2209–12. http://dx.doi.org/10.1016/j.tetasy.2004.04.014.

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33

Lavoie, Christopher M., and Mark Stradiotto. "Bisphosphines: A Prominent Ancillary Ligand Class for Application in Nickel-Catalyzed C–N Cross-Coupling." ACS Catalysis 8, no. 8 (June 20, 2018): 7228–50. http://dx.doi.org/10.1021/acscatal.8b01879.

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34

Baba, Katsuaki, Yoshihiro Masuya, Naoto Chatani, and Mamoru Tobisu. "Palladium-catalyzed Cyclization of Bisphosphines to Phosphacycles via the Cleavage of Two Carbon–Phosphorus Bonds." Chemistry Letters 46, no. 9 (September 5, 2017): 1296–99. http://dx.doi.org/10.1246/cl.170581.

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35

MCKINSTRY, L., and T. LIVINGHOUSE. "ChemInform Abstract: An Efficient Procedure for the Synthesis of Electron-Rich Bisphosphines Containing Homochiral Backbones." ChemInform 26, no. 19 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199519168.

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36

Prades, Amparo, Samuel Núñez-Pertíñez, Antoni Riera, and Xavier Verdaguer. "P-Stereogenic bisphosphines with a hydrazine backbone: from N–N atropoisomerism to double nitrogen inversion." Chemical Communications 53, no. 33 (2017): 4605–8. http://dx.doi.org/10.1039/c7cc01944k.

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37

Fujimoto, Hayato, Momoka Kusano, Takuya Kodama, and Mamoru Tobisu. "Cyclization of Bisphosphines to Phosphacycles via the Cleavage of Two Carbon–Phosphorus Bonds by Nickel Catalysis." Organic Letters 21, no. 11 (May 22, 2019): 4177–81. http://dx.doi.org/10.1021/acs.orglett.9b01355.

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38

Shi, Shi-Liang, Li-Wen Xu, Kounosuke Oisaki, Motomu Kanai, and Masakatsu Shibasaki. "Identification of Modular Chiral Bisphosphines Effective for Cu(I)-Catalyzed Asymmetric Allylation and Propargylation of Ketones." Journal of the American Chemical Society 132, no. 19 (May 19, 2010): 6638–39. http://dx.doi.org/10.1021/ja101948s.

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39

Takahashi, Kohei, Makoto Yamashita, Yoshiyuki Tanaka, and Kyoko Nozaki. "Ruthenium/C5Me5/Bisphosphine- or Bisphosphite-Based Catalysts fornormal-Selective Hydroformylation." Angewandte Chemie 124, no. 18 (March 21, 2012): 4459–63. http://dx.doi.org/10.1002/ange.201108396.

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40

Takahashi, Kohei, Makoto Yamashita, Yoshiyuki Tanaka, and Kyoko Nozaki. "Ruthenium/C5Me5/Bisphosphine- or Bisphosphite-Based Catalysts fornormal-Selective Hydroformylation." Angewandte Chemie International Edition 51, no. 18 (March 21, 2012): 4383–87. http://dx.doi.org/10.1002/anie.201108396.

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41

Bhat, Sajad A., Joel T. Mague, and Maravanji S. Balakrishna. "Synthesis, structural and photoluminescence studies of copper(I) complexes containing bis(azol-1-yl)methane derived bisphosphines." Polyhedron 107 (March 2016): 190–95. http://dx.doi.org/10.1016/j.poly.2016.01.032.

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42

Paladino, Giuseppe, David Madec, Guillaume Prestat, Guillaume Maitro, Giovanni Poli, and Anny Jutand. "Oxidative Addition of Ligand-Chelated Palladium(0) to Aryl Halides: Comparison between 1,2-Bisthioethers and 1,2-Bisphosphines." Organometallics 26, no. 2 (January 2007): 455–58. http://dx.doi.org/10.1021/om060846x.

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43

Zhang, Zhaoguo, Hu Qian, James Longmire, and Xumu Zhang. "Synthesis of Chiral Bisphosphines with Tunable Bite Angles and Their Applications in Asymmetric Hydrogenation of β-Ketoesters." Journal of Organic Chemistry 65, no. 19 (September 2000): 6223–26. http://dx.doi.org/10.1021/jo000462v.

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44

Bhat, Sajad A., Joel T. Mague, and Maravanji S. Balakrishna. "Synthesis and structural characterization of copper(I) halide complexes containing bis(azol-1-yl)methane derived bisphosphines." Inorganica Chimica Acta 443 (March 2016): 243–50. http://dx.doi.org/10.1016/j.ica.2016.01.010.

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45

Andersen, Neil G., Masood Parvez, Robert McDonald, and Brian A. Keay. "Synthesis, resolution, and application of 2,2′-bis(diphenylphosphino)-3,3′-binaphtho[b]furan (BINAPFu)." Canadian Journal of Chemistry 82, no. 2 (February 1, 2004): 145–61. http://dx.doi.org/10.1139/v03-173.

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(±)-2,2′-Bis(diphenylphosphino)-3,3′-binaphtho[2,1-b]furan (BINAPFu) was synthesized from 2-naphthoxyacetic acid in a five-step sequence in 62% overall yield. A variety of reported resolution procedures for biaryl bisphosphines did not work with (±)-BINAPFu; thus, a new resolution method was developed, involving the Staudinger reaction of the aforementioned racemate of BINAPFu with an enantiopure camphor sulfonyl azide derivative. The resulting diastereomeric phosphinimines were separated by flash chromatography. Subsequent hydrolysis to the corresponding bis-phosphine oxide and trichlorosilane reduction provided enantiopure BINAPFu. The absolute stereochemical configuration of BINAPFu was established by X-ray crystallography. BINAPFu was compared with commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP) in Pd(0)-catalyzed intermolecular Heck reactions. Investigation of the Heck arylation of 2,3-dihydrofuran showed BINAPFu to be more efficacious than BINAP in dioxane at 30 °C. A variety of phosphorus selenides were prepared, and the 1JP-Se coupling constants measured, to obtain a comparative scale of parent phosphine basicity. The phosphorus atoms in BINAPFu were found to be electron deficient when compared with BINAP but slightly more electron rich than trifurylphosphine. Key words: naphthofurans, atropisomers, electron-deficient phosphines, asymmetric Heck reactions, Staudinger reaction.

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46

Musina, Elvira I., Tatiana I. Wittmann, Igor D. Strelnik, Olga E. Naumova, Andrey A. Karasik, Dmitry B. Krivolapov, Daut R. Islamov, et al. "Influence of the rac–meso isomerization of seven-membered cyclic bisphosphines on the predominant formation of chelate complexes." Polyhedron 100 (November 2015): 344–50. http://dx.doi.org/10.1016/j.poly.2015.08.033.

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47

Bhat, Sajad A., Joel T. Mague, and Maravanji S. Balakrishna. "Transition metal chemistry of large-bite bisphosphines, N,N-bis(diphenylphosphinobenzyl)-N-phenylamine and bis(2-diphenylphosphinobenzyl)ether." Journal of Organometallic Chemistry 809 (May 2016): 21–30. http://dx.doi.org/10.1016/j.jorganchem.2016.02.020.

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48

Greb, Lutz, Pascual Oña-Burgos, Adam Kubas, Florian C. Falk, Frank Breher, Karin Fink, and Jan Paradies. "[2.2]Paracyclophane derived bisphosphines for the activation of hydrogen by FLPs: application in domino hydrosilylation/hydrogenation of enones." Dalton Transactions 41, no. 30 (2012): 9056. http://dx.doi.org/10.1039/c2dt30374d.

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49

Tomsu, Gerald, Matthias Mastalir, Ernst Pittenauer, Berthold Stöger, Günter Allmaier, and Karl Kirchner. "Ligand-Enforced Switch of the Coordination Mode in Low-Valent Group 6 Carbonyl Complexes Containing Pyrimidine-Based Bisphosphines." Organometallics 37, no. 12 (June 4, 2018): 1919–26. http://dx.doi.org/10.1021/acs.organomet.8b00192.

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50

Bhat, Sajad A., Joel T. Mague, and Maravanji S. Balakrishna. "Mononuclear, Tetranuclear and 1D Polymeric Copper(I) Complexes of Large Bite Bisphosphines Containing Nitrogen and Oxygen Donor Atoms." European Journal of Inorganic Chemistry 2015, no. 23 (July 17, 2015): 3949–58. http://dx.doi.org/10.1002/ejic.201500418.

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