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Journal articles on the topic 'Phosphine – Synthesis'

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Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Gusarova, Nina K., Svetlana N. Arbuzova, and Boris A. Trofimov. "Novel general halogen-free methodology for the synthesis of organophosphorus compounds." Pure and Applied Chemistry 84, no. 3 (January 17, 2012): 439–59. http://dx.doi.org/10.1351/pac-con-11-07-11.

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The use of novel general halogen-free methodology for the synthesis of phosphines, phosphine chalcogenides, and phosphinic acids from elemental phosphorus and alkenes and alkynes in the superbase suspensions is described.

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2

Ghosh, Sujit, Kinkar Biswas, and Basudeb Basu. "Recent Advances in Microwave Promoted C-P Cross-coupling Reactions." Current Microwave Chemistry 7, no. 2 (August 6, 2020): 112–22. http://dx.doi.org/10.2174/2213335607666200401144724.

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: Organophosphorous compounds are of potential importance in diverse fields. They are often used as intermediates for making functionalized phosphine ligands as well as find vast applications in the areas of industrial, agricultural and biological chemistry. The microwave-assisted synthesis of C-P bonds has become increasingly popular because of its various advantages over conventional heating in the perspectives of green chemistry. : This review article has primarily focused on the synthesis of various organophosphorous molecules via microwave promoted C-P cross-coupling reactions under metal-catalyzed or metal–free conditions over the last two decades. The synthesis of phosphine ligands on 4,4′-bisquinolone structural framework, disubstituted phosphinic acid esters, vinyl phosphines, aryl- and vinylphosphonates, sugar and nucleoside phosphonates, aminobisphosphonates, triphenyl phosphines, water-soluble tertiary phosphine oxides and many other potentially useful organophosphorous compounds have been illustrated critically. The Hirao reaction, Michaelis-Arbuzov reaction and Sandmeyer type of reactions are generally involved in creating C-P bonds. The role of various metal catalysts, solvents, bases, additives and temperature in different literatures are carefully discussed.

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3

Das, Mrinal K., Sarbari Roy, H. Noth, and A. Pidcock. "Synthesis and Characterization of Some Phosphine-Boranes and Phosphine- and Phosphite-Cyanoboranes." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 16, no. 1 (January 1986): 67–75. http://dx.doi.org/10.1080/00945718608055911.

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4

Alonso, Concepción, Endika Martín-Encinas, Gloria Rubiales, and Francisco Palacios. "Reliable Synthesis of Phosphino- and Phosphine Sulfide-1,2,3,4-Tetrahydroquinolines and Phosphine Sulfide Quinolines." European Journal of Organic Chemistry 2017, no. 20 (May 26, 2017): 2916–24. http://dx.doi.org/10.1002/ejoc.201700258.

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5

Pereira, Mariette M., Mário J. F. Calvete, Rui M. B. Carrilho, and Artur R. Abreu. "Synthesis of binaphthyl based phosphine and phosphite ligands." Chemical Society Reviews 42, no. 16 (2013): 6990. http://dx.doi.org/10.1039/c3cs60116a.

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6

Gusarova, N. K., S. N. Arbusova, S. F. Malysheva, M. Ya Khil'ko, A. A. Tatarinova, V. G. Gorokhov, and B. A. Trofimov. "Synthesis of primary phosphines from phosphine and arylethylenes." Russian Chemical Bulletin 44, no. 8 (August 1995): 1535. http://dx.doi.org/10.1007/bf00714449.

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7

Munzeiwa, Wisdom A., Bernard Omondi, and Vincent O. Nyamori. "Architecture and synthesis of P,N-heterocyclic phosphine ligands." Beilstein Journal of Organic Chemistry 16 (March 12, 2020): 362–83. http://dx.doi.org/10.3762/bjoc.16.35.

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Diverse P,N-phosphine ligands reported to date have performed exceptionally well as auxiliary ligands in organometallic catalysis. Phosphines bearing 2-pyridyl moieties prominently feature in literature as compared to phosphines with five-membered N-heterocycles. This discussion seeks to paint a broad picture and consolidate different synthetic protocols and techniques for N-heterocyclic phosphine motifs. The introduction provides an account of P,N-phosphine ligands, and their structural and coordination benefits from combining heteroatoms with different basicity in one ligand. The body discusses the synthetic protocols which focus on P–C, P–N-bond formation, substrate and nucleophile types and different N-heterocycle construction strategies. Selected references are given in relation to the applications of the ligands.

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8

Chahma, M'hamed, Daniel JT Myles, and Robin G. Hicks. "Synthesis, characterization, and coordination chemistry of phosphines with ethylenedioxythiophene substituents." Canadian Journal of Chemistry 83, no. 2 (February 1, 2005): 150–55. http://dx.doi.org/10.1139/v05-004.

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The preparation of several new phosphines bearing one or more 3,4-ethylenedioxythiophene (EDOT) units as substituents linked at the 2-thienyl position is described. The phosphines were prepared by reaction of lithiated EDOT intermediates with appropriate chlorophosphines to afford (3,4-ethylenedioxy-2-thienyl)diphenylphosphine (1), (bis(3,4-ethylenedioxy-2-thienyl)phenylphosphine (2), tris(3,4-ethylenedioxy-2-thienyl)phosphine (3), 2,5-bis(diphenylphosphino)-3,4-ethylenedioxythiophene (4), and 2-diphenylphosphino-5-mesitylthio-3,4-ethylenedioxythiophene (5). Molybdenum carbonyl complexes of compounds 13 were prepared by reaction of the phosphine ligands with cis-Mo(CO)4(pip)2. In all cases, spectroscopic evidence is fully consistent with the phosphines acting as monodentate, P-bound ligands. Electrochemical studies on the phosphines as well as their metal complexes indicate that the normal electrochemical redox robustness of the EDOT group is dramatically decreased by the presence of phosphine substituents: all compounds exhibited irreversible oxidation processes and no evidence of electropolymerization was observed for the phosphines bearing two or three EDOT groups. Key words: phosphines, thiophene, 3,4-ethylenedioxythiophene, EDOT, electrochemistry, coordination complexes.

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9

Pedroarena, James R., Bryan P. Nell, Lev N. Zakharov, and David R. Tyler. "Synthesis of Unsymmetrical Bis(phosphine) Oxides and Their Phosphines via Secondary Phosphine Oxide Precursors." Journal of Inorganic and Organometallic Polymers and Materials 30, no. 1 (August 21, 2019): 196–205. http://dx.doi.org/10.1007/s10904-019-01288-9.

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10

Schmalz, Hans-Günther, Mehmet Dindaroğlu, and Anna Falk. "A Scalable Synthesis of Chiral Modular Phosphine-Phosphite Ligands." Synthesis 45, no. 04 (January 18, 2013): 527–35. http://dx.doi.org/10.1055/s-0032-1316847.

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11

Jia, Xian, Xingshu Li, Wing Sze Lam, Stanton H. L. Kok, Lijin Xu, Gui Lu, Chi-Hung Yeung, and Albert S. C. Chan. "The synthesis of new chiral phosphine–phosphinites, phosphine–phosphoramidite, and phosphine–phosphite ligands and their applications in asymmetric hydrogenation." Tetrahedron: Asymmetry 15, no. 14 (July 2004): 2273–78. http://dx.doi.org/10.1016/j.tetasy.2004.05.046.

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12

Trofimov, Boris, Nina Gusarova, and Nataliya Chernysheva. "Catalyst- and Solvent-Free Addition of the P–H Species to Alkenes and Alkynes: A Green Methodology for C–P Bond Formation." Synthesis 49, no. 21 (August 28, 2017): 4783–807. http://dx.doi.org/10.1055/s-0036-1588542.

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Traditional methods for C–P bond formation via direct addition of P–H species to unsaturated compounds are usually implemented in the presence of base and metal catalysts or radical initiators in various organic solvents. During the last five years, a novel efficient and general catalyst/initiator- and solvent-free version of the hydrophosphination and hydrophosphinylation of multiple C–C bonds with H-phosphines and their chalcogenides has begun to develop and it is attracting growing attention. This approach corresponds to the recently emerged pot-, atom-, and step-economy (PASE) green paradigm. This review covers the literature on the synthesis of useful and in-demand organophosphorus compounds via catalyst- and solvent-free addition of P–H species to alkenes and alkynes.1 Introduction2 Addition of Secondary Phosphines to Alkenes3 Hydrophosphinylation of Alkenes with Secondary Phosphine Chalcogenides3.1 Oxidative Addition of Phosphine Oxides to Vinyl Sulfides3.2 Addition of Secondary Phosphine Sulfides and Phosphine Selenides to Alkenes3.3 Addition of Secondary Phosphine Sulfides and Phosphine Selenides to Divinyl Chalcogenides3.4 Hydrophosphinylation of Alkenes with Secondary Phosphine/Chalcogen Pair (Three-Component Reactions)4 Addition of Secondary Phosphines to Alkynes5 Addition of Secondary Phosphine Chalcogenides to Alkynes6 Conclusion

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13

Reeves, Brian J., and Brycelyn M. Boardman. "Synthesis and characterization of thienyl phosphines and thienyl phosphine chalcogenides." Polyhedron 73 (May 2014): 118–23. http://dx.doi.org/10.1016/j.poly.2014.02.030.

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14

GUSAROVA, N. K., S. N. ARBUZOVA, S. F. MALYSHEVA, M. YA KHIL'KO, A. A. TATARINOVA, V. G. GOROKHOV, and B. A. TROFIMOV. "ChemInform Abstract: Synthesis of Primary Phosphines from Phosphine and Arylethylenes." ChemInform 26, no. 50 (August 16, 2010): no. http://dx.doi.org/10.1002/chin.199550149.

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15

Pereira, Mariette M., Mario J. F. Calvete, Rui M. B. Carrilho, and Artur R. Abreu. "ChemInform Abstract: Synthesis of Binaphthyl Based Phosphine and Phosphite Ligands." ChemInform 44, no. 42 (October 1, 2013): no. http://dx.doi.org/10.1002/chin.201342225.

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16

Eisler, Dana J., and Richard J. Puddephatt. "Synthesis and conformations of phosphine- and phosphinite-derivatized resorcinarenes." Canadian Journal of Chemistry 82, no. 2 (February 1, 2004): 185–94. http://dx.doi.org/10.1139/v03-105.

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The synthesis of resorcinarene derivatives with four or eight alkynyldiphenylphosphine or diphenyl phosphinite functional groups is reported. The tetraphosphinite derivatives have effective C2v symmetry and have the potential to adopt two different boat conformations in which the arene groups with phosphinite substituents are horizontal or vertical. A method for the determination of the solution-state conformation of the resorcinarene skeleton using correlated 1H and 13C NMR data is reported, and the boat conformation of one tetraphosphinite compound in the solid state has been determined crystallographically.Key words: phosphine, phosphinite, resorcinarene, conformation.

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17

Matsumura, Mio, Mizuki Yamada, Atsuya Muranaka, Misae Kanai, Naoki Kakusawa, Daisuke Hashizume, Masanobu Uchiyama, and Shuji Yasuike. "Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives." Beilstein Journal of Organic Chemistry 13 (October 30, 2017): 2304–9. http://dx.doi.org/10.3762/bjoc.13.226.

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The parent benzophospholo[3,2-b]indole was prepared by the reaction of dichlorophenylphosphine with a dilithium intermediate, which was prepared in two steps from 2-ethynyl-N,N-dimethylaniline. Using the obtained benzophosphole-fused indole as a common starting material, simple modifications were carried out at the phosphorus center of the phosphole, synthesizing various functionalized analogs. The X-ray structure analysis of trivalent phosphole and phosphine oxide showed that the fused tetracyclic moieties are planar. The benzophosphole-fused indoles, such as phosphine oxide, phospholium salt, and borane complex, exhibited strong photoluminescence in dichloromethane (Φ = 67–75%).

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18

Wu, Lie, Shi Bian, Hao Huang, Jiahong Wang, Danni Liu, Paul K. Chu, and Xue-Feng Yu. "Black Phosphorus: An Effective Feedstock for the Synthesis of Phosphorus-Based Chemicals." CCS Chemistry 1, no. 2 (June 2019): 166–72. http://dx.doi.org/10.31635/ccschem.019.20180013.

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We propose and demonstrate the novel concept of synthesizing organophosphorus compounds directly from black phosphorus (BP) nanoparticles as the feedstock. Compounds such as alkyl phosphines, alkyl phosphine oxides, phosphine sulfide, and hexafluorophosphate anion are prepared with good isolation yields under mild conditions. Selective synthesis of primary, secondary, and tertiary organophosphorus compounds is also demonstrated utilizing this one-pot approach. Reaction mechanisms are proposed and discussed. Compared with traditional white phosphorus (P4)-based methods, the new synthetic concept and process utilizing elemental phosphorus are more efficient and environmentally friendly.

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19

Tajti, Szatmári, Perdih, Keglevich, and Bálint. "Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component." Molecules 24, no. 8 (April 25, 2019): 1640. http://dx.doi.org/10.3390/molecules24081640.

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In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik–Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyethyl-αaminophosphonate derivatives was optimized in respect of the temperature, the reaction time, and the molar ratio of the starting materials. A few by-products were also identified. N,NBis(phosphinoylmethyl)amines containing a hydroxyethyl group were also prepared by the double Kabachnik–Fields reaction of ethanolamine with an excess of paraformaldehyde and secondary phosphine oxides. The crystal structure of a 2-hydroxyethyl-α-aminophosphine oxide and a bis(phosphinoylmethyl)ethanolamine was studied by X-ray analysis.

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20

Gao, Yuzhen, Xueqin Li, Jian Xu, Yile Wu, Weizhu Chen, Guo Tang, and Yufen Zhao. "Mn(OAc)3-mediated phosphonation–lactonization of alkenoic acids: synthesis of phosphono-γ-butyrolactones." Chemical Communications 51, no. 9 (2015): 1605–7. http://dx.doi.org/10.1039/c4cc07978g.

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A new, general method for the synthesis of phosphono-γ-butyrolactones has been achieved through Mn(OAc)₃-mediated radical oxidative phosphonation and lactonization of alkenoic acids withH-phosphonates andH-phosphine oxide.

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21

Kolesinska, Beata. "P-Acylphosphonium salts and their vinyloges — application in synthesis." Open Chemistry 8, no. 6 (December 1, 2010): 1147–71. http://dx.doi.org/10.2478/s11532-010-0114-z.

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AbstractReview with 101 refs. of progress in synthetic applications and properties of P-acylphosphonium salts including acylation via P-acylphosphonium salts, enantioselective acylation using chiral phosphine ligands, nucleophilic (β)-oniovinylation, and reaction involving vinyloges of P-acylphosphonium salts formed by treatment conjugated alkenoates or alkynoates with phosphines.

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22

Imamoto, Tsuneo, Toshiyuki Oshiki, Takashi Onozawa, Tetsuo Kusumoto, and Kazuhiko Sato. "Synthesis and reactions of phosphine-boranes. Synthesis of new bidentate ligands with homochiral phosphine centers via optically pure phosphine-boranes." Journal of the American Chemical Society 112, no. 13 (June 1990): 5244–52. http://dx.doi.org/10.1021/ja00169a036.

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23

Stará, Irena G., Angelina Andronova, Adrian Kollárovič, Štěpán Vyskočil, Sylvain Jugé, Guy C. Lloyd-Jones, Patrick J. Guiry, and Ivo Starý. "Enantioselective [2+2+2] cycloisomerisation of alkynes in the synthesis of helicenes: The search for effective chiral ligands." Collection of Czechoslovak Chemical Communications 76, no. 12 (2011): 2005–22. http://dx.doi.org/10.1135/cccc2011177.

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The enantioselective [2+2+2] cycloisomerisation of the aromatic triynes under nickel(0) catalysis to afford nonracemic [6]- and [7]helicene derivatives has been systematically studied. A collection of mono- and bidentate phosphines, phosphites, phosphinites and phosphinous amides possessing stereogenic units such as chiral centre, axis or plane (or their combinations) has been tested and axially chiral binaphthyl-derived monodentate MOP-type phosphine ligands were the optimal class of ligands. Nickel complexes of these ligands afforded nonracemic tetrahydro[6]helicene in up to 64% ee in a model reaction.

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24

Miao, Shiding, Stephen G. Hickey, Christian Waurisch, Vladimir Lesnyak, Tobias Otto, Bernd Rellinghaus, and Alexander Eychmüller. "Synthesis of Monodisperse Cadmium Phosphide Nanoparticles Using ex-Situ Produced Phosphine." ACS Nano 6, no. 8 (July 17, 2012): 7059–65. http://dx.doi.org/10.1021/nn3021037.

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25

Heutz, Frank J. L., and Paul C. J. Kamer. "Modular solid-phase synthesis, catalytic application and efficient recycling of supported phosphine–phosphite ligand libraries." Dalton Transactions 45, no. 5 (2016): 2116–23. http://dx.doi.org/10.1039/c5dt03226a.

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26

Wang, Xian-Liang, Jin-Xiang Chen, Xue-Shun Jia, and Liang Yin. "Synthesis of α,β-Unsaturated Phosphine Sulfides." Synthesis 52, no. 01 (September 30, 2019): 141–49. http://dx.doi.org/10.1055/s-0039-1690685.

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α,β-Unsaturated phosphine sulfides may exhibit different reactivity from α,β-unsaturated phosphine oxides toward nucleophilic addition and thus may find new applications in copper(I)-catalyzed asymmetric reactions. Herein, various α,β-unsaturated phosphine sulfides were prepared in moderate to excellent yields from the parent α,β-unsaturated phosphine oxides with Lawesson’s reagent. The reaction enjoys a broad substrate scope and tolerates a variety of functional groups.

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27

Gusarova, N. K., S. F. Malysheva, S. N. Arbuzova, and B. A. Trofimov. "Synthesis of organic phosphines and phosphine oxides from elemental phosphorus and phosphine in the presence of strong bases." Russian Chemical Bulletin 47, no. 9 (September 1998): 1645–52. http://dx.doi.org/10.1007/bf02495680.

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28

Itazaki, Masumi, Shinya Katsube, Masahiro Kamitani, and Hiroshi Nakazawa. "Synthesis of vinylphosphines and unsymmetric diphosphines: iron-catalyzed selective hydrophosphination reaction of alkynes and vinylphosphines with secondary phosphines." Chemical Communications 52, no. 15 (2016): 3163–66. http://dx.doi.org/10.1039/c5cc10185a.

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29

IMAMOTO, Tsuneo. "Synthesis and Reactions of Phosphine-Boranes." Journal of Synthetic Organic Chemistry, Japan 51, no. 3 (1993): 223–31. http://dx.doi.org/10.5059/yukigoseikyokaishi.51.223.

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30

Camps, Pelayo, Gisela Colet, Sergi Segura, and Santiago Vázquez. "Synthesis of new cyclopentane phosphine oxides." Arkivoc 2007, no. 4 (May 18, 2006): 8–19. http://dx.doi.org/10.3998/ark.5550190.0008.402.

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31

Shapley, Patricia A., Robert M. Marshman, Jeanine M. Shusta, Zewdu Gebeyehu, and Scott R. Wilson. "Synthesis of Nitridoosmium(VI) Phosphine Complexes." Inorganic Chemistry 33, no. 3 (February 1994): 498–502. http://dx.doi.org/10.1021/ic00081a017.

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32

Hayashi, T., T. Nishimura, S. Hirabayashi, and Y. Yasuhara. "Synthesis of Chiral Allylic Phosphine Oxides." Synfacts 2006, no. 6 (June 2006): 0575. http://dx.doi.org/10.1055/s-2006-934475.

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33

Mehta, Meera, Timothy C. Johnstone, Jolie Lam, Bidraha Bagh, André Hermannsdorfer, Matthias Driess, and Douglas W. Stephan. "Synthesis and oxidation of phosphine cations." Dalton Trans. 46, no. 41 (2017): 14149–57. http://dx.doi.org/10.1039/c7dt03175k.

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Cationic phosphines of the form [(L)PPh₂]⁺ are prepared from Ph₂PCl and carbenes (L), including a chiral bis(oxazoline)-based carbene, a cyclic(alkyl)(amino) carbene, and a 1,2,3-triazolium-derived carbene. A related dication was prepared from PhPCl₂ and a bis-carbene. The monocations, but not the dication, can be oxidized with XeF₂.

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34

Hornillos, Valentín, Carlos Vila, Edwin Otten, and Ben L. Feringa. "Catalytic Asymmetric Synthesis of Phosphine Boronates." Angewandte Chemie 127, no. 27 (May 7, 2015): 7978–82. http://dx.doi.org/10.1002/ange.201502987.

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35

Hornillos, Valentín, Carlos Vila, Edwin Otten, and Ben L. Feringa. "Catalytic Asymmetric Synthesis of Phosphine Boronates." Angewandte Chemie International Edition 54, no. 27 (May 7, 2015): 7867–71. http://dx.doi.org/10.1002/anie.201502987.

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36

Jasieniak, Jacek, Craig Bullen, Joel van Embden, and Paul Mulvaney. "Phosphine-Free Synthesis of CdSe Nanocrystals." Journal of Physical Chemistry B 109, no. 44 (November 2005): 20665–68. http://dx.doi.org/10.1021/jp054289o.

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37

Huszthy, Péter, Hajnalka Szabó-Szentjóbi, István Majoros, Anna Márton, Ibolya Leveles, Beáta G. Vértessy, Miklós Dékány, and Tünde Tóth. "Synthesis of New Chiral Crown Ethers Containing Phosphine or Secondary Phosphine Oxide Units." Synthesis 52, no. 19 (June 10, 2020): 2870–82. http://dx.doi.org/10.1055/s-0040-1707854.

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The transition-metal complexes of phosphine and secondary phosphine oxide compounds can be used in various catalytic reactions. In this paper, the synthesis and characterization of eight new crown ethers containing trivalent phosphorus in their macroring are reported. These macrocycles are promising candidates as ligands for catalytic reactions.

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38

Tokairin, Yoshinori, Hiroyuki Konno, Angéline Noireau, Caroline West, Hiroki Moriwaki, Vadim A. Soloshonok, Cyril Nicolas, and Isabelle Gillaizeau. "Asymmetric synthesis of the two enantiomers of β-phosphorus-containing α-amino acids via hydrophosphinylation and hydrophosphonylation of chiral Ni(ii)-complexes." Organic Chemistry Frontiers 8, no. 10 (2021): 2190–95. http://dx.doi.org/10.1039/d1qo00159k.

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A new approach for the synthesis of the two enantiomers of β-phosphorus-containing α-amino acids was developed via Michael addition of secondary phosphine oxides and dialkyl phosphites to chiral Ni(ii)-complexes of a dehydroalanine-Schiff base.

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39

Huang, Xiaofeng, Yanfu Wei, Tao Zhou, Yangsong Qin, Kunyang Gao, and Xinyue Ding. "Synthesis of tetrakis (hydroxymethyl) phosphonium chloride by high-concentration phosphine in industrial off-gas." Water Science and Technology 68, no. 2 (July 1, 2013): 342–47. http://dx.doi.org/10.2166/wst.2013.240.

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With increasing consumption of phosphate rock and acceleration of global phosphate production, the shortage of phosphate resources is increasing with the development and utilization of phosphate. China's Ministry of Land and Resources has classified phosphate as a mineral that cannot meet China's growing demand for phosphate rock in 2010. The phosphorus chemical industry is one of the important economic pillars for Yunnan province. Yellow phosphorus production in enterprises has led to a significant increase in the amount of phosphorus sludge. This paper focuses on phosphine generation in the process of phosphoric sludge utilization, where the flame retardant tetrakis (hydroxymethyl) phosphonium chloride (THPC) is synthesized by high concentrations of phosphine. The optimum conditions are determined at a space velocity of 150 h−1, a reaction temperature of 60 °C, 0.75 g of catalyst, and a ratio of raw materials of 4:1. Because of the catalytic oxidation of copper chloride (CuCl2), the synthesis of THPC was accelerated significantly. In conclusion, THPC can be efficiently synthesized under optimal conditions and with CuCl2 as a catalyst.

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40

Jung, Chan Su, Kidong Park, Yeron Lee, In Hye Kwak, Ik Seon Kwon, Jundong Kim, Jaemin Seo, Jae-Pyoung Ahn, and Jeunghee Park. "Nickel phosphide polymorphs with an active (001) surface as excellent catalysts for water splitting." CrystEngComm 21, no. 7 (2019): 1143–49. http://dx.doi.org/10.1039/c8ce01884g.

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We report the temperature-controlled synthesis of two nickel phosphide polymorphs, Ni₂P and Ni₅P₄, by phosphorization of Ni foil or foams using phosphine gas, and their excellent catalytic activity toward hydrogen evolution reaction.

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41

Demchuk, Oleg M., Katarzyna Kielar, and K. Michał Pietrusiewicz. "Rational design of novel ligands for environmentally benign cross-coupling reactions." Pure and Applied Chemistry 83, no. 3 (January 31, 2011): 633–44. http://dx.doi.org/10.1351/pac-con-10-08-06.

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Transition-metal (TM) complexes of new phosphines, readily prepared by a straight-forward three-step modular synthesis, were successfully employed in difficult cross-coupling reactions conducted under mild conditions (water, “open-flask”, low temperature) that aspire to meet green chemistry criteria. High yielding catalyzed by bismuth or rhodium complexes oxidative arylation of naphthoquinone gave the key 2-arylnaphthoquinone intermediates for facile bismuth triflate-catalyzed Michael addition of secondary phosphine oxides. Subsequent O-methylation and reductions of the resulting products gave access to the target air-stable phosphine ligands in good overall yields (up to 60 %).

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42

Eren, Nimrod M., Samantha A. Orr, Christopher D. Thompson, Emily C. Border, Michael A. Stevens, and Victoria L. Blair. "Synthesis, Structure, and Solution Studies of Lithiated Allylic Phosphines and Phosphine Oxides." Organometallics 39, no. 11 (May 26, 2020): 2080–90. http://dx.doi.org/10.1021/acs.organomet.0c00144.

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43

Agh-Atabay, N., F. M. Ashmawy, C. A. McAuliffe, and W. E. Hill. "Synthesis and characterisation of oxotungsten(VI) complexes of phosphines and phosphine oxides." Inorganica Chimica Acta 104, no. 2 (October 1985): 73–76. http://dx.doi.org/10.1016/s0020-1693(00)86418-x.

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44

Bayardon, Jérôme, Julie Bernard, Emmanuelle Rémond, Yoann Rousselin, Raluca Malacea-Kabbara, and Sylvain Jugé. "Efficient Synthesis of (P-Chirogenic) o-Boronated Phosphines from sec-Phosphine Boranes." Organic Letters 17, no. 5 (February 13, 2015): 1216–19. http://dx.doi.org/10.1021/acs.orglett.5b00167.

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Babu, Boppudi Hari, Gandavaram Syam Prasad, Chamarthi Naga Raju, and Mandava Venkata Basaveswara Rao. "Synthesis of Phosphonates via Michaelis-Arbuzov Reaction." Current Organic Synthesis 14, no. 6 (September 28, 2017): 883–903. http://dx.doi.org/10.2174/1570179414666161230144455.

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Background: Michaelis–Arbuzov reaction has played a key role for the synthesis of dialkyl or diaryl phosphonates by reacting various alkyl or aryl halides with trialkyl or triaryl phosphite. This reaction is very versatile in the formation of P-C bond from the reaction of aliphatic halides with phosphinites or phosphites to yield phosphonates, phosphinates, phosphine oxides. The Arbuzov reaction developed some methodologies, possible mechanistic pathways, selectivity, potential applications and biologically active various phosphonates. Objective: The synthesis of phosphonates via Michaelis–Arbuzov reaction with many new and fascinating methodologies were developed and disclosed in the literature, and these are explored in this review. Conclusion: This review has discussed past developments and vast potential applications of Arbuzov reaction in the synthesis of organophosphonates. As presented in this review, various synthetic methodologies were developed to prepare a large variety of phosphonates. Improvements in the reaction conditions of Lewis-acid mediated Arbuzov rearrangement as well as the development of MW-assisted Arbuzov rearrangement were discussed. Finally, to achieve high selectivities and yields, fine-tuning of reaction conditions including solvent type, temperature, and optimal reaction times to be considered.

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Grushin, Vladimir V. "Catalysis for Catalysis: Synthesis of Mixed Phosphine−Phosphine Oxide Ligands via Highly Selective, Pd-Catalyzed Monooxidation of Bidentate Phosphines." Journal of the American Chemical Society 121, no. 24 (June 1999): 5831–32. http://dx.doi.org/10.1021/ja990841+.

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Shen, Ruwei, Ming Zhang, Jing Xiao, Chao Dong, and Li-Biao Han. "Ph3P-mediated highly selective C(α)–P coupling of quinone monoacetals with R2P(O)H: convenient and practical synthesis of ortho-phosphinyl phenols." Green Chemistry 20, no. 22 (2018): 5111–16. http://dx.doi.org/10.1039/c8gc02918k.

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The Ph₃P-mediated C(α)–P coupling reaction of quinone monoacetals with secondary phosphine oxides is developed to provide an effective method for the synthesis of a wide array of ortho-phosphinyl phenols in good to excellent yields.

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Clarke, Celia, Stéphanie Foussat, David J. Fox, Daniel Sejer Pedersen, and Stuart Warren. "Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes." Org. Biomol. Chem. 7, no. 7 (2009): 1323–28. http://dx.doi.org/10.1039/b817433d.

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Ren, Wei, Qian-Ming Zuo, and Shang-Dong Yang. "NHC-Catalyzed Synthesis of Benzazole-Phosphine Ligands under an Air Atmosphere." Synlett 30, no. 14 (July 24, 2019): 1719–24. http://dx.doi.org/10.1055/s-0037-1610723.

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An efficient strategy for the synthesis of benzazole-phosphine ligand precursors via N-heterocyclic carbene catalyzed aerobic oxidative cyclization reaction has been performed. The reaction displays broad functional group tolerance and high atom economy, and the transformation has been further applied to benzazole-phosphine ligand synthesis.

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Khabiyev, A. T., and B. S. Selenova. "Palladium(II)-catalyzed Suzuki–Miyaura Reactions of Arylboronic Acid with Aryl Halide in the Presence of Aryl-Ferrocenyl-Phosphines." Eurasian Chemico-Technological Journal 16, no. 1 (December 22, 2013): 79. http://dx.doi.org/10.18321/ectj172.

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<p>This study examined investigation of catalytic activity of aryl-ferrocenyl-phosphine (2-methoxyphenyl diferrocenyl phosphine (cat. 1), 2-tert-butyloxyphenyl diferrocenyl phosphine (cat. 2), 2-methoxynaphtyl diferrocenyl phosphine (cat. 3), 1,1’-bis(diphenylphosphino) ferrocene (cat. 4), phenyl diferrocenyl phosphine (cat. 5)) ligands with palladium salts as precursors in Suzuki–Miyaura reaction. Suzuki–Miyaura reaction is one of the important cross-coupling reactions and extremely powerful in forming C–C bonds. Aryl-ferrocenyl-phosphine ligands confer unprecedented activity for these processes, allowing reactions to be performed at low catalyst levels, to prepare extreme This study examined investigation of catalytic activity of aryl-ferrocenyl-phosphine (2-methoxyphenyl diferrocenyl phosphine (cat. 1), 2-tert-butyloxyphenyl diferrocenyl phosphine (cat. 2), 2-methoxynaphtyl diferrocenyl phosphine (cat. 3), 1,1’-bis(diphenylphosphino) ferrocene (cat. 4), phenyl diferrocenyl phosphine (cat. 5)) ligands with palladium salts as precursors in Suzuki–Miyaura reaction. Suzuki–Miyaura reaction is one of the important cross-coupling reactions and extremely powerful in forming C–C bonds. Aryl-ferrocenyl-phosphine ligands confer unprecedented activity for these processes, allowing reactions to be performed at low catalyst levels, to prepare extremely hindered biaryls and to be carried out, in general, also for reactions of aryl chlorides by temperature 100 ºC and pressure 1 atm. Sterically demanding and strongly Lewis-basic ferrocene-based phosphines are water- and oxygen-resistant. The Suzuki–Miyaura reaction is also an important reaction in the ground and fine organic synthesis, in the production of drugs and intermediates. To analyze the conversion of halogen aryl compounds the <sup>1</sup>H NMR spectroscopy was used. The advantage of Suzuki–Miyaura reaction in comparison with other cross-coupling reactions (Kumada-, Heck-, Heck-Carbonylation-, Murahashi-, Sonogashira-, Negishi-, Stille-reaktion, etc.) is in the usage of low toxic, water- and oxygen-insensitive thermostable organoboron compounds. As boronic acid was used phenylboronic acid and as weak base – potassium phosphate. Catalyst, precursor and weak base were dissolved in toluene. All reactions were performed under an atmosphere of nitrogen or argon. The catalytic cycle of Suzuki–Miyaura reaction typically includes three main steps: oxidative addition of the haloaromatic to catalytic active palladium (0) species, transmetalation, and reductive elimination of the product under back formation of catalytically active species. All used catalysts showed good activity with aryl bromides and weak activity with aryl chlorides.</p>

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