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Journal articles on the topic 'C-P Bond Formation'

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Author: Grafiati

Published: 6 September 2023

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1

Li, Lili, Wenbin Huang, Lijin Chen, Jiaxing Dong, Xuebing Ma, and Yungui Peng. "Silver-Catalyzed Oxidative C(sp3 )−P Bond Formation through C−C and P−H Bond Cleavage." Angewandte Chemie 129, no. 35 (July 21, 2017): 10675–80. http://dx.doi.org/10.1002/ange.201704910.

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2

Li, Lili, Wenbin Huang, Lijin Chen, Jiaxing Dong, Xuebing Ma, and Yungui Peng. "Silver-Catalyzed Oxidative C(sp3 )−P Bond Formation through C−C and P−H Bond Cleavage." Angewandte Chemie International Edition 56, no. 35 (July 21, 2017): 10539–44. http://dx.doi.org/10.1002/anie.201704910.

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3

Zagidullin, Almaz A., Il’yas F. Sakhapov, Vasili A. Miluykov, and Dmitry G. Yakhvarov. "Nickel Complexes in C‒P Bond Formation." Molecules 26, no. 17 (August 31, 2021): 5283. http://dx.doi.org/10.3390/molecules26175283.

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This review is a comprehensive account of reactions with the participation of nickel complexes that result in the formation of carbon–phosphorus (C‒P) bonds. The catalytic and non-catalytic reactions with the participation of nickel complexes as the catalysts and the reagents are described. The various classes of starting compounds and the products formed are discussed individually. The several putative mechanisms of the nickel catalysed reactions are also included, thereby providing insights into both the synthetic and the mechanistic aspects of this phosphorus chemistry.

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4

Budnikova, Yulia H., Tatyana V. Gryaznova, Valeriya V. Grinenko, Yulia B. Dudkina, and Mikhail N. Khrizanforov. "Eco-efficient electrocatalytic C–P bond formation." Pure and Applied Chemistry 89, no. 3 (March 1, 2017): 311–30. http://dx.doi.org/10.1515/pac-2016-1001.

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AbstractThe development of practical, efficient and atom-economical methods of formation of carbon-phosphorus bonds remains a topic of considerable interest for the current synthetic organic chemistry and electrochemistry. This review summarizes selected topics from the recent publications with particular emphasis on phosphine and phosphine oxides formation from white phosphorus, chlorophosphines in electrocatalytic processes using aryl, hetaryl or perfluoroalkyl halides as reagents. This review includes selected highlights concerning recent progress in modification of catalytic systems for aromatic C–H bonds phosphonation involving metal-catalyzed ligand directed or metal-induced oxidative processes. Furthermore, a part of this review is devoted to phosphorylation of olefins with white phosphorus under reductive conditions in water-organic media. Finally, we have also documented recent advances in ferrocene C–H activation and phosphorylation.

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5

Wauters, Iris, Wouter Debrouwer, and Christian V. Stevens. "Preparation of phosphines through C–P bond formation." Beilstein Journal of Organic Chemistry 10 (May 9, 2014): 1064–96. http://dx.doi.org/10.3762/bjoc.10.106.

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Phosphines are an important class of ligands in the field of metal-catalysis. This has spurred the development of new routes toward functionalized phosphines. Some of the most important C–P bond formation strategies were reviewed and organized according to the hybridization of carbon in the newly formed C–P bond.

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6

HIDAKA, Tomomi, and Haruo SETO. "Studies on C-P Bond Forming Enzymes. Biochemical Mechanisms of C-P Bond Formation in Bialaphos." Journal of the agricultural chemical society of Japan 65, no. 10 (1991): 1497–500. http://dx.doi.org/10.1271/nogeikagaku1924.65.1497.

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7

Cai, Bao-Gui, Jun Xuan, and Wen-Jing Xiao. "Visible light-mediated C P bond formation reactions." Science Bulletin 64, no. 5 (March 2019): 337–50. http://dx.doi.org/10.1016/j.scib.2019.02.002.

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8

Khrizanforov, M. N., S. O. Strekalova, V. V. Grinenko, A. I. Kononov, E. L. Dolengovski, and Y. H. Budnikova. "C-P bond formation via selective electrocatalytic C-H phosphorylation." Phosphorus, Sulfur, and Silicon and the Related Elements 194, no. 4-6 (January 9, 2019): 384–85. http://dx.doi.org/10.1080/10426507.2018.1555538.

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9

Onys'ko, Petro, Yuliya Rassukana, and Anatoly Sinitsa. "Phosphorylation of α-Haloimines: P-C vs. P-N Bond Formation." Current Organic Chemistry 12, no. 1 (January 1, 2008): 2–24. http://dx.doi.org/10.2174/138527208783330091.

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10

Hidaka, Tomomi, Kazuma Kamigiri, Satoshi Imai, and Haruo Seto. "Biosynthetic Mechanisms of C-P Bond Formation of Bialaphos." Actinomycetologica 5, no. 2 (1991): 112–18. http://dx.doi.org/10.3209/saj.5_112.

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11

Borger, Jaap E., Andreas W. Ehlers, J. Chris Slootweg, and Koop Lammertsma. "Functionalization of P4 through Direct P−C Bond Formation." Chemistry - A European Journal 23, no. 49 (July 27, 2017): 11738–46. http://dx.doi.org/10.1002/chem.201702067.

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12

Zhang, Ji-Shu, Tieqiao Chen, Jia Yang, and Li-Biao Han. "Nickel-catalysed P–C bond formation via P–H/C–CN cross coupling reactions." Chemical Communications 51, no. 35 (2015): 7540–42. http://dx.doi.org/10.1039/c5cc01182e.

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Nickel-catalysed P–H/C–CN cross coupling reactions take place efficiently under mild reaction conditions affording the corresponding sp²C–P bonds. This transformation provides a convenient method for the preparation of both arylphosphines and arylphosphine oxides from the readily available P–H compounds and arylnitriles.

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13

Chen, Lijin, Zhenfei Zhou, Saifei Zhang, Xiaoqian Li, Xuebing Ma, and Jiaxing Dong. "Palladium(ii)-catalyzed oxidative C(sp3)–P bond formation via C(sp3)–H bond activation." Chemical Communications 55, no. 91 (2019): 13693–96. http://dx.doi.org/10.1039/c9cc07637a.

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14

Hari, Durga Prasad, and Burkhard König. "Eosin Y Catalyzed Visible Light Oxidative C–C and C–P bond Formation." Organic Letters 13, no. 15 (August 5, 2011): 3852–55. http://dx.doi.org/10.1021/ol201376v.

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15

Geer, Ana M., Ángel L. Serrano, Bas de Bruin, Miguel A. Ciriano, and Cristina Tejel. "Terminal Phosphanido Rhodium Complexes Mediating Catalytic PP and PC Bond Formation." Angewandte Chemie 127, no. 2 (November 19, 2014): 482–85. http://dx.doi.org/10.1002/ange.201407707.

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16

Banerjee, Indrani, and Tarun K. Panda. "Recent advances in the carbon–phosphorus (C–P) bond formation from unsaturated compounds by s- and p-block metals." Organic & Biomolecular Chemistry 19, no. 30 (2021): 6571–87. http://dx.doi.org/10.1039/d1ob01019k.

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A detailed discussion on the catalytic addition of P–H bonds from various phosphine reagents to unsaturated bonds for the C–P bond formation promoted by various s- and p-block metal catalysts is reported.

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17

HIDAKA, Tomomi, Osamu KARA, Satoshi IMAI, Hiroyuki ANZAI, Takeshi MURAKAMI, Kozo NAGAOKA, and Haruo SETO. "Biochemical mechanism of C-P bond formation of bialaphos: Use of gene manipulation for the analysis of the C-P bond formation step." Agricultural and Biological Chemistry 54, no. 8 (1990): 2121–25. http://dx.doi.org/10.1271/bbb1961.54.2121.

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18

Hidaka, Tomomi, Osamu Hara, Satoshi Imai, Hiroyuki Anzai, Takeshi Murakami, Kozo Nagaoka, and Haruo Seto. "Biochemical Mechanism of C–P Bond Formation of Bialaphos: Use of Gene Manipulation for the Analysis of the C–P Bond Formation Step." Agricultural and Biological Chemistry 54, no. 8 (August 1990): 2121–25. http://dx.doi.org/10.1080/00021369.1990.10870254.

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19

Yorimitsu, Hideki. "Homolytic substitution at phosphorus for C–P bond formation in organic synthesis." Beilstein Journal of Organic Chemistry 9 (June 28, 2013): 1269–77. http://dx.doi.org/10.3762/bjoc.9.143.

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Organophosphorus compounds are important in organic chemistry. This review article covers emerging, powerful synthetic approaches to organophosphorus compounds by homolytic substitution at phosphorus with a carbon-centered radical. Phosphination reagents include diphosphines, chalcogenophosphines and stannylphosphines, which bear a weak P–heteroatom bond for homolysis. This article deals with two transformations, radical phosphination by addition across unsaturated C–C bonds and substitution of organic halides.

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20

Zhao, Xiuli, Mengmeng Huang, Yabo Li, Jianye Zhang, Jung Keun Kim, and Yangjie Wu. "Stepwise photosensitized C(sp3)–C(CO) bond cleavage and C–P bond formation of 1,3-dicarbonyls with arylphosphine oxides." Organic Chemistry Frontiers 6, no. 9 (2019): 1433–37. http://dx.doi.org/10.1039/c9qo00075e.

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21

Valentini, Federica, Oriana Piermatti, and Luigi Vaccaro. "Metal and Metal Oxide Nanoparticles Catalyzed C–H Activation for C–O and C–X (X = Halogen, B, P, S, Se) Bond Formation." Catalysts 13, no. 1 (December 22, 2022): 16. http://dx.doi.org/10.3390/catal13010016.

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The direct functionalization of an inactivated C–H bond has become an attractive approach to evolve toward step-economy, atom-efficient and environmentally sustainable processes. In this regard, the design and preparation of highly active metal nanoparticles as efficient catalysts for C–H bond activation under mild reaction conditions still continue to be investigated. This review focuses on the functionalization of un-activated C(sp3)–H, C(sp2)–H and C(sp)–H bonds exploiting metal and metal oxide nanoparticles C–H activation for C–O and C–X (X = Halogen, B, P, S, Se) bond formation, resulting in more sustainable access to industrial production.

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22

Xie, Peizhong, Lei Guo, Lanlan Xu, and Teck-Peng Loh. "Asymmetric P−C Bond Formation: Diastereoselective Synthesis of Adjacent P,C-Stereogenic Allylic Phosphorus Compounds." Chemistry - An Asian Journal 11, no. 9 (March 29, 2016): 1353–56. http://dx.doi.org/10.1002/asia.201600108.

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23

Wicht, Denyce K., Igor V. Kourkine, Ivan Kovacik, David S. Glueck, Thomas E. Concolino, Glenn P. A. Yap, Christopher D. Incarvito, and Arnold L. Rheingold. "Platinum-Catalyzed Acrylonitrile Hydrophosphination. P−C Bond Formation via Olefin Insertion into a Pt−P Bond." Organometallics 18, no. 25 (December 1999): 5381–94. http://dx.doi.org/10.1021/om990745h.

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24

Hidaka, Tomomi, and Haruo Seto. "Studies on the C-P Bond Formation Mechanisms in Bialaphos." Actinomycetologica 6, no. 2 (1992): 105–12. http://dx.doi.org/10.3209/saj.6_105.

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25

Jayaraman, Arumugam, Tyler V. Jacob, Jeff Bisskey, and Brian T. Sterenberg. "Sequential electrophilic P–C bond formation in metal-coordinated chlorophosphines." Dalton Transactions 44, no. 19 (2015): 8788–91. http://dx.doi.org/10.1039/c5dt01281c.

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26

Hidaka, T., S. Imai, O. Hara, H. Anzai, T. Murakami, K. Nagaoka, and H. Seto. "Carboxyphosphonoenolpyruvate phosphonomutase, a novel enzyme catalyzing C-P bond formation." Journal of Bacteriology 172, no. 6 (1990): 3066–72. http://dx.doi.org/10.1128/jb.172.6.3066-3072.1990.

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27

Hosseinian, Akram, Fatemeh Alsadat Hosseini Nasab, Sheida Ahmadi, Zahra Rahmani, and Esmail Vessally. "Decarboxylative cross-coupling reactions for P(O)–C bond formation." RSC Advances 8, no. 46 (2018): 26383–98. http://dx.doi.org/10.1039/c8ra04557g.

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Phosphorus-containing compounds are one of the most important classes of organic compounds, which have wide applications in organic chemistry, medicinal chemistry, agricultural chemistry, and materials chemistry.

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28

Yang, Shang-Dong, and Ya-Min Li. "New Strategies for Transition-Metal-Catalyzed C-P Bond Formation." Synlett 24, no. 14 (July 26, 2013): 1739–44. http://dx.doi.org/10.1055/s-0033-1339341.

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29

Zhang, Hui, Xue-Yan Zhang, Dao-Qing Dong, and Zu-Li Wang. "Copper-catalyzed cross-coupling reactions for C–P bond formation." RSC Advances 5, no. 65 (2015): 52824–31. http://dx.doi.org/10.1039/c5ra08858e.

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30

Wauters, Iris, Wouter Debrouwer, and Christian V. Stevens. "ChemInform Abstract: Preparation of Phosphines Through C-P Bond Formation." ChemInform 46, no. 14 (March 19, 2015): no. http://dx.doi.org/10.1002/chin.201514320.

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31

Heinl, Sebastian, Sabine Reisinger, Christoph Schwarzmaier, Michael Bodensteiner, and Manfred Scheer. "Selective Functionalization of P4by Metal-Mediated CP Bond Formation." Angewandte Chemie International Edition 53, no. 29 (May 30, 2014): 7639–42. http://dx.doi.org/10.1002/anie.201403295.

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32

Jablonkai, Erzsebet, and Gyorgy Keglevich. "ChemInform Abstract: P-C Bond Formation by Coupling Reactions Utilizing." ChemInform 45, no. 34 (August 7, 2014): no. http://dx.doi.org/10.1002/chin.201434255.

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33

Li, Yuanming, Shyamal Chakrabarty, Christian Mück-Lichtenfeld, and Armido Studer. "Ortho -Trialkylstannyl Arylphosphanes by C-P and C-Sn Bond Formation in Arynes." Angewandte Chemie International Edition 55, no. 2 (December 3, 2015): 802–6. http://dx.doi.org/10.1002/anie.201509329.

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34

Zhang, Ji-Shu, Tieqiao Chen, Jia Yang, and Li-Biao Han. "ChemInform Abstract: Nickel-Catalyzed P-C Bond Formation via P-H/C-CN Cross Coupling Reactions." ChemInform 46, no. 34 (August 2015): no. http://dx.doi.org/10.1002/chin.201534225.

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35

Zhang, Bo, Constantin Gabriel Daniliuc, and Armido Studer. "6-Phosphorylated Phenanthridines from 2-Isocyanobiphenyls via Radical C–P and C–C Bond Formation." Organic Letters 16, no. 1 (December 9, 2013): 250–53. http://dx.doi.org/10.1021/ol403256e.

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36

Hari, Durga Prasad, and Burkhard Koenig. "ChemInform Abstract: Eosin Y Catalyzed Visible Light Oxidative C-C and C-P Bond Formation." ChemInform 42, no. 50 (November 17, 2011): no. http://dx.doi.org/10.1002/chin.201150136.

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37

Wan, Boshun, Haolong Wang, Xincheng Li, and Fan Wu. "Direct Oxidative C-P Bond Formation of Indoles with Dialkyl Phosphites." Synthesis 44, no. 06 (February 14, 2012): 941–45. http://dx.doi.org/10.1055/s-0031-1289700.

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38

Giffin, Kaitie A., Lorraine A. Pua, Ilia Korobkov, and R. Tom Baker. "Formation and C–F bond functionalization of [P,N]-ligated perfluoronickelacyclopentanes." Polyhedron 157 (January 2019): 458–66. http://dx.doi.org/10.1016/j.poly.2018.10.024.

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39

Isshiki, Ryota, Kei Muto, and Junichiro Yamaguchi. "Decarbonylative C–P Bond Formation Using Aromatic Esters and Organophosphorus Compounds." Organic Letters 20, no. 4 (February 2, 2018): 1150–53. http://dx.doi.org/10.1021/acs.orglett.8b00080.

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40

Zhang, Yan, and Chengjian Zhu. "Gold complex-catalyzed C P bond formation by Kabachnik–Fields reactions." Catalysis Communications 28 (November 2012): 134–37. http://dx.doi.org/10.1016/j.catcom.2012.08.001.

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41

Glueck, David S. "ChemInform Abstract: Recent Advances in Metal-Catalyzed C-P- Bond Formation." ChemInform 42, no. 18 (April 7, 2011): no. http://dx.doi.org/10.1002/chin.201118202.

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42

Blum, Ofer, Felix Frolow, and David Milstein. "C–F bond activation by iridium(I). A unique process involving P–C bond cleavage, P–F bond formation and net retention of oxidation state." J. Chem. Soc., Chem. Commun., no. 4 (1991): 258–59. http://dx.doi.org/10.1039/c39910000258.

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43

Das, Deepankar, and Daniel Seidel. "Redox-Neutral α-C–H Bond Functionalization of Secondary Amines with Concurrent C–P Bond Formation/N-Alkylation." Organic Letters 15, no. 17 (August 19, 2013): 4358–61. http://dx.doi.org/10.1021/ol401858k.

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44

Li, Chong, Juan Wang, and Shang-Dong Yang. "Visible-light-facilitated P-center radical addition to CX (X = C, N) bonds results in cyclizations." Chemical Communications 57, no. 65 (2021): 7997–8002. http://dx.doi.org/10.1039/d1cc02604f.

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45

Xiong, Yunkui, Jianye Zhang, Liping Qi, Yu Zhang, and Tao Wang. "Oxidative C(SP2)‐P Formation: Direct Construction of C‐P Bond on Quinoxalines via Aromatic Phosphorous Oxide." ChemistrySelect 6, no. 4 (January 25, 2021): 657–62. http://dx.doi.org/10.1002/slct.202004036.

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46

Diaz, Armando A., Bryan Buster, Daniel Schomisch, Masood A. Khan, J. Clayton Baum, and Rudolf J. Wehmschulte. "Size Matters: Room Temperature P−C Bond Formation Through C−H Activation inm-Terphenyldiiodophosphines." Inorganic Chemistry 47, no. 7 (April 2008): 2858–63. http://dx.doi.org/10.1021/ic702105s.

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47

Blades, Kevin, Sunita T. Patel, Jonathan M. Percy, and Robin D. Wilkes. "Facile [2,3]-rearrangements of difluoroallylic alcohols with CP and CS bond formation." Tetrahedron Letters 37, no. 35 (August 1996): 6403–6. http://dx.doi.org/10.1016/0040-4039(96)01358-5.

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48

Srinivas, Katam, and Ganesan Prabusankar. "Role of C, S, Se and P donor ligands in copper(i) mediated C–N and C–Si bond formation reactions." RSC Advances 8, no. 56 (2018): 32269–82. http://dx.doi.org/10.1039/c8ra06057f.

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49

Li, Xue, Tieqiao Chen, Yuta Saga, and Li-Biao Han. "Iron-catalyzed cross coupling of P–H/C–O bonds: efficient synthesis of α-alkoxyphosphorus compounds." Dalton Transactions 45, no. 5 (2016): 1877–80. http://dx.doi.org/10.1039/c5dt02454d.

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An efficient P–C bond-formation through iron-catalyzed cross coupling of P–H/C–O bonds is developed for the first time. This reaction proceeds efficiently to produce the corresponding valuable α-alkoxyphosphorus compounds under mild conditions with a wide generality.

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50

Keweloh, Lukas, Niklas Aders, Alexander Hepp, Damian Pleschka, Ernst-Ulrich Würthwein, and Werner Uhl. "A P–H functionalized Al/P-based frustrated Lewis pair – hydrophosphination of nitriles, ring opening with cyclopropenones and evidence of PC double bond formation." Dalton Transactions 47, no. 25 (2018): 8402–17. http://dx.doi.org/10.1039/c8dt01836g.

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