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Journal articles on the topic 'Palladium precatalysts'

Author: Grafiati

Published: 4 June 2021

Last updated: 14 February 2022

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1

Takahashi, Rina, Koji Kubota, and Hajime Ito. "Air- and moisture-stable Xantphos-ligated palladium dialkyl complex as a precatalyst for cross-coupling reactions." Chemical Communications 56, no. 3 (2020): 407–10. http://dx.doi.org/10.1039/c9cc06946a.

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A Xantphos-ligated palladium dialkyl complex can serve as a high performance precatalyst for various cross-coupling reactions, thus providing a convenient alternative to previously developed classes of precatalysts.

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2

Martin, Anthony R., Anthony Chartoire, Alexandra M. Z. Slawin, and Steven P. Nolan. "Extending the utility of [Pd(NHC)(cinnamyl)Cl] precatalysts: Direct arylation of heterocycles." Beilstein Journal of Organic Chemistry 8 (September 27, 2012): 1637–43. http://dx.doi.org/10.3762/bjoc.8.187.

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The use of [Pd(NHC)(cinnamyl)Cl] precatalysts in the direct arylation of heterocycles has been investigated. Among four different precatalysts, [Pd(SIPr)(cinnamyl)Cl] proved to be the most efficient promoter of the reaction. The C–H functionalization of sulfur- or nitrogen-containing heterocycles has been achieved at low catalyst loadings. These catalyst charges range from 0.1 to 0.01 mol % palladium.

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3

Marchenko, Anatoliy, Georgyi Koidan, Anastasiya Hurieva, Yurii Vlasenko, Aleksandr Kostyuk, and Andrea Biffis. "Palladium(ii) complexes with chelating N-phosphanyl acyclic diaminocarbenes: synthesis, characterization and catalytic performance in Suzuki couplings." Dalton Transactions 45, no. 5 (2016): 1967–75. http://dx.doi.org/10.1039/c5dt02250a.

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4

Arthurs, Ross A., David L. Hughes, and Christopher J. Richards. "Planar chiral palladacycle precatalysts for asymmetric synthesis." Organic & Biomolecular Chemistry 18, no. 28 (2020): 5466–72. http://dx.doi.org/10.1039/d0ob01331e.

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5

Bigler, Raphael, Daniel Spiess, Joël Wellauer, Martin Binder, Victor Carré, and Serena Fantasia. "Synthesis of Biaryl Phosphine Palladium(0) Precatalysts." Organometallics 40, no. 15 (July 6, 2021): 2384–88. http://dx.doi.org/10.1021/acs.organomet.1c00288.

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6

Yang, Yong, Joyce Fen Yan Lim, Xinying Chew, Edward G. Robins, Charles W. Johannes, Yee Hwee Lim, and Howard Jong. "Palladium precatalysts containing meta-terarylphosphine ligands for expedient copper-free Sonogashira cross-coupling reactions." Catalysis Science & Technology 5, no. 7 (2015): 3501–6. http://dx.doi.org/10.1039/c5cy00507h.

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Novel precatalysts containing meta-terarylphosphine ligands have set a new standard for high performance and practicality in copper-free Sonogashira cross-coupling catalysis using simple and reliable protocols.

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7

Vásquez-Céspedes, Suhelen, Michael Holtkamp, Uwe Karst, and Frank Glorius. "Reusable and Magnetic Palladium and Copper Oxide Catalysts in Direct ortho and meta Arylation of Anilide Derivatives." Synlett 28, no. 20 (May 2, 2017): 2759–64. http://dx.doi.org/10.1055/s-0036-1589007.

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We report a general, direct C–H arylation of anilide derivatives using reusable palladium or copper oxide on magnetite as heterogeneous precatalysts. Highly selective ortho and meta arylations are achieved using electronically and sterically diverse diaryliodonium salts. Catalytically active soluble species from the heterogeneous precursors were detected by experimental techniques. Preliminary mechanistic investigation suggests different reaction pathways for each of the catalysts.

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8

Jahnke, Mareike C., Tania Pape, and F. Ekkehardt Hahn. "Molecular Structures and Catalytic Activity of Palladium Complexes Derived from Lutidine-bridged Bis(benzimidazolin-2-ylidene) Ligands." Zeitschrift für Naturforschung B 62, no. 3 (March 1, 2007): 357–61. http://dx.doi.org/10.1515/znb-2007-0308.

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Reaction of lutidine-bridged dibenzimidazolium dibromides 1 - 4 with palladium acetate gives pincer-type palladium complexes of the type [Pd(L)Br]Br [5]Br-[8]Br. Crystals suitable for an X-ray diffraction study have been obtained by slow evaporation of the solvent from dichloromethane/methanol solutions of [7]Br and [8]Br. The crystal structure of [7]+ reveals a pincer topology of the cationic complex with a distorted square-planar coordination geometry at the metal center. From a solution of complex [8]Br, a dinuclear byproduct [9]+ was obtained with two bis(benzimidazolin- 2-ylidene) ligands coordinating in a bridging fashion. The pincer-type palladium complexes [5]Br- [8]Br were tested as precatalysts in Suzuki coupling reactions.

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9

Zhang, Fei-Yi, Xiao-Bing Lan, Chang Xu, Hua-Gang Yao, Tian Li, and Feng-Shou Liu. "Rigid hindered N-heterocyclic carbene palladium precatalysts: synthesis, characterization and catalytic amination." Organic Chemistry Frontiers 6, no. 18 (2019): 3292–99. http://dx.doi.org/10.1039/c9qo00726a.

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Rigid hindered N-heterocyclic carbene palladium complexes have been developed and exhibited high activities for a variety of (hetero)aryl chlorides with (hetero)anilines and amines under aerobic conditions.

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10

Biffis, Andrea, Elena Scattolin, Nicoletta Ravasio, and Federica Zaccheria. "Supported copper precatalysts for ligand-free, palladium-free Sonogashira coupling reactions." Tetrahedron Letters 48, no. 49 (December 2007): 8761–64. http://dx.doi.org/10.1016/j.tetlet.2007.10.005.

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11

Shaughnessy, Kevin H. "Development of Palladium Precatalysts that Efficiently Generate LPd(0) Active Species." Israel Journal of Chemistry 60, no. 3-4 (September 4, 2019): 180–94. http://dx.doi.org/10.1002/ijch.201900067.

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12

Chen, Fu-Min, Dong-Dong Lu, Li-Qun Hu, Ju Huang, and Feng-Shou Liu. "Camphyl-based α-diimine palladium complexes: highly efficient precatalysts for direct arylation of thiazoles in open-air." Organic & Biomolecular Chemistry 15, no. 27 (2017): 5731–36. http://dx.doi.org/10.1039/c7ob00856b.

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13

Chatterjee, Anamitra, Sondre H. Hopen Eliasson, Karl W. Törnroos, and Vidar R. Jensen. "Palladium Precatalysts for Decarbonylative Dehydration of Fatty Acids to Linear Alpha Olefins." ACS Catalysis 6, no. 11 (October 17, 2016): 7784–89. http://dx.doi.org/10.1021/acscatal.6b02460.

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14

Marion, Nicolas, and Steven P. Nolan. "Well-Defined N-Heterocyclic Carbenes−Palladium(II) Precatalysts for Cross-Coupling Reactions." Accounts of Chemical Research 41, no. 11 (November 18, 2008): 1440–49. http://dx.doi.org/10.1021/ar800020y.

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15

Hu, Huaiyuan, Ashley M. Gilliam, Fengrui Qu, and Kevin H. Shaughnessy. "Enolizable Ketones as Activators of Palladium(II) Precatalysts in Amine Arylation Reactions." ACS Catalysis 10, no. 7 (March 6, 2020): 4127–35. http://dx.doi.org/10.1021/acscatal.0c00221.

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16

Rama, Raquel J., Celia Maya, and M. Carmen Nicasio. "Dialkylterphenyl Phosphine‐Based Palladium Precatalysts for Efficient Aryl Amination of N ‐Nucleophiles." Chemistry – A European Journal 26, no. 5 (January 16, 2020): 1064–73. http://dx.doi.org/10.1002/chem.201903279.

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17

Balogh, Janos, Antsar Rih Hlil, Ibrahim El-Zoghbi, Muhammad Ghufran Rafique, Dalila Chouikhi, Mohammed Al-Hashimi, and Hassan S. Bazzi. "Phase-Separable Polyisobutylene Palladium-PEPPSI Precatalysts: Synthesis and Application in Buchwald-Hartwig Amination." Macromolecular Rapid Communications 38, no. 15 (June 19, 2017): 1700214. http://dx.doi.org/10.1002/marc.201700214.

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18

Espinosa, Matthew R., Angelino Doppiu, and Nilay Hazari. "Differences in the Performance of Allyl Based Palladium Precatalysts for Suzuki‐Miyaura Reactions." Advanced Synthesis & Catalysis 362, no. 22 (September 17, 2020): 5062–78. http://dx.doi.org/10.1002/adsc.202000987.

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19

Chartoire, Anthony, Mathieu Lesieur, Alexandra M. Z. Slawin, Steven P. Nolan, and Catherine S. J. Cazin. "Highly Active Well-Defined Palladium Precatalysts for the Efficient Amination of Aryl Chlorides." Organometallics 30, no. 16 (August 22, 2011): 4432–36. http://dx.doi.org/10.1021/om2005222.

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20

Wuttke, Evelyn, Bettina Nägele, Bernhard Weibert, and Florian Kessler. "Palladium Alkynyl and Allenylidene Complexes: Very Efficient Precatalysts for C–C Coupling Reactions." Organometallics 30, no. 22 (November 28, 2011): 6270–82. http://dx.doi.org/10.1021/om200862m.

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21

Lin, Yong-Chieh, Hsin-Hsueh Hsueh, Shanker Kanne, Li-Kuang Chang, Fu-Chen Liu, Ivan J. B. Lin, Gene-Hsiang Lee, and Shie-Ming Peng. "Efficient PEPPSI-Themed Palladium N-Heterocyclic Carbene Precatalysts for the Mizoroki–Heck Reaction." Organometallics 32, no. 14 (June 28, 2013): 3859–69. http://dx.doi.org/10.1021/om4003297.

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22

Hu, Tao, Yan-Guo Li, Yue-Sheng Li, and Ning-Hai Hu. "Novel highly active binuclear neutral nickel and palladium complexes as precatalysts for norbornene polymerization." Journal of Molecular Catalysis A: Chemical 253, no. 1-2 (July 2006): 155–64. http://dx.doi.org/10.1016/j.molcata.2006.03.008.

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23

Shu, Wei, and Stephen L. Buchwald. "Use of precatalysts greatly facilitate palladium-catalyzed alkynylations in batch and continuous-flow conditions." Chemical Science 2, no. 12 (2011): 2321. http://dx.doi.org/10.1039/c1sc00409c.

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24

Baier, Heiko, Philipp Metzner, Thomas Körzdörfer, Alexandra Kelling, and Hans-Jürgen Holdt. "Efficient Palladium(II) Precatalysts Bearing 4,5-Dicyanoimidazol-2-ylidene for the Mizoroki-Heck Reaction." European Journal of Inorganic Chemistry 2014, no. 18 (May 20, 2014): 2952–60. http://dx.doi.org/10.1002/ejic.201402040.

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25

Astruc, Didier. "Palladium Nanoparticles as Efficient Green Homogeneous and Heterogeneous Carbon−Carbon Coupling Precatalysts: A Unifying View." Inorganic Chemistry 46, no. 6 (March 2007): 1884–94. http://dx.doi.org/10.1021/ic062183h.

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26

Hu, Li-Qun, Rong-Li Deng, Yan-Fen Li, Cui-Jin Zeng, Dong-Sheng Shen, and Feng-Shou Liu. "Developing Bis(imino)acenaphthene-Supported N-Heterocyclic Carbene Palladium Precatalysts for Direct Arylation of Azoles." Organometallics 37, no. 2 (January 5, 2018): 214–26. http://dx.doi.org/10.1021/acs.organomet.7b00784.

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27

Suijkerbuijk, Bart M. J. M., Sara D. Herreras Martínez, Gerard van Koten, and Robertus J. M. Klein Gebbink. "Hetero-multimetallic Tetrakis(SCS-pincer palladium)−(Metallo)porphyrin Hybrids. Tunable Precatalysts in a Heck Reaction." Organometallics 27, no. 4 (February 2008): 534–42. http://dx.doi.org/10.1021/om7005613.

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28

Bruno, Nicholas C., and Stephen L. Buchwald. "Synthesis and Application of Palladium Precatalysts that Accommodate Extremely Bulky Di-tert-butylphosphino Biaryl Ligands." Organic Letters 15, no. 11 (May 15, 2013): 2876–79. http://dx.doi.org/10.1021/ol401208t.

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29

Matano, Yoshihiro, Kazuaki Matsumoto, Tarou Shibano, and Hiroshi Imahori. "Porphyrin-appended phosphapalladacycle precatalysts: effects of central metals on the catalytic activity in a high-temperature Heck reaction." Journal of Porphyrins and Phthalocyanines 15, no. 11n12 (November 2011): 1172–82. http://dx.doi.org/10.1142/s1088424611004087.

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The synthesis and the catalytic activity of bis(μ-chloro)-bridged, phosphapalladacycle-fused diporphyrins (M-porphyrin-appended phosphapalladacycles: M = Zn , Ni , free-base), as well as the coordinating ability of their precursors, meso-phosphanylporphyrins are reported. Treatment of meso-phosphanylporphyrinatozinc(II) with an equimolar amount of PdCl2(NCPh)2 caused regioselective β-C–H activation of the porphyrin ring to produce bis(μ-chloro)-bridged Zn -porphyrin-appended phosphapalladacycle, which was further converted to the free-base- and Ni -porphyrin-appended analogs. The UV-vis absorption spectra of these palladium complexes showed weak exciton coupling between two porphyrin chromophores connected by the μ-chloro bridges. The M-porphyrin-appended phosphapalladacycles behaved as precatalysts for a high temperature Heck reaction between p-bromobenzaldehyde and butyl acrylate. In a range of the catalyst-loading of 0.05–0.005 mol.%, the catalytic activity was found to significantly depend on the central metal incorporated at the porphyrin core. The Ni -porphyrin-appended phosphapalladacycle showed considerably higher turnover frequency than did the Zn -porphyrin- and free-base-porphyrin-appended counterparts. This trend in the catalytic activity does not simply correlate with the σ-donating ability of the phosphorus center and the electron-donating ability of the porphyrin π-systems. Instead, it is related to the durability of the precatalysts under the reaction conditions employed. The observed results corroborate that the central metal of the meso-phosphanylporphyrin ligands plays a crucial role in the active Pd(0) catalyst-loading from the porphyrin-appended phosphapalladacycles at constant efficiency.

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30

Zhao, Yu, Alex J. Nett, Anne J. McNeil, and Paul M. Zimmerman. "Computational Mechanism for Initiation and Growth of Poly(3-hexylthiophene) Using Palladium N-Heterocyclic Carbene Precatalysts." Macromolecules 49, no. 20 (October 4, 2016): 7632–41. http://dx.doi.org/10.1021/acs.macromol.6b01648.

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31

Bruno, Nicholas C., Matthew T. Tudge, and Stephen L. Buchwald. "Design and preparation of new palladium precatalysts for C–C and C–N cross-coupling reactions." Chem. Sci. 4, no. 3 (2013): 916–20. http://dx.doi.org/10.1039/c2sc20903a.

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32

Kirschning, Andreas, Wladimir Solodenko, Klaas Mennecke, Carla Vogt, and Susan Gruhl. "Polyvinylpyridine, a Versatile Solid Phase for Coordinative Immobilisation of Palladium Precatalysts - Applications in Suzuki-Miyaura Reactions." Synthesis 2006, no. 11 (June 2006): 1873–81. http://dx.doi.org/10.1055/s-2006-942370.

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33

Zeng, Yanning, Qaiser Mahmood, Qiuyue Zhang, Tongling Liang, and Wen-Hua Sun. "Vinyl homo/copolymerization of norbornene and ethylene using sterically enhanced 1,2-bis(arylimino)acenaphthene-palladium precatalysts." Journal of Polymer Science Part A: Polymer Chemistry 56, no. 8 (February 9, 2018): 922–30. http://dx.doi.org/10.1002/pola.28970.

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34

Shu, Wei, and Stephen L. Buchwald. "ChemInform Abstract: Use of Precatalysts Greatly Facilitate Palladium-Catalyzed Alkynylations in Batch and Continuous-Flow Conditions." ChemInform 43, no. 13 (March 1, 2012): no. http://dx.doi.org/10.1002/chin.201213070.

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35

Zeng, Yanning, Qaiser Mahmood, Qiuyue Zhang, Tongling Liang, and Wen-Hua Sun. "Highly thermo-stable and electronically controlled palladium precatalysts for vinyl homo/co-polymerization of norbornene-ethylene." European Polymer Journal 103 (June 2018): 342–50. http://dx.doi.org/10.1016/j.eurpolymj.2018.04.028.

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36

Bruno, Nicholas C., and Stephen L. Buchwald. "ChemInform Abstract: Synthesis and Application of Palladium Precatalysts that Accommodate Extremely Bulky Di-tert-butylphosphino Biaryl Ligands." ChemInform 44, no. 40 (September 12, 2013): no. http://dx.doi.org/10.1002/chin.201340062.

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37

Christmann, Ute, Dimitrios A. Pantazis, Jordi Benet-Buchholz, John E. McGrady, Feliu Maseras, and Ramón Vilar. "Experimental and Theoretical Investigations of New Dinuclear Palladium Complexes as Precatalysts for the Amination of Aryl Chlorides." Journal of the American Chemical Society 128, no. 19 (May 2006): 6376–90. http://dx.doi.org/10.1021/ja057825z.

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38

John, Alex, Mobin M. Shaikh, and Prasenjit Ghosh. "Suzuki–Miyaura cross-coupling of aryl chlorides catalyzed by palladium precatalysts of N/O-functionalized pyrazolyl ligands." Inorganica Chimica Acta 363, no. 12 (October 2010): 3113–21. http://dx.doi.org/10.1016/j.ica.2010.04.006.

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39

Denisov, M. S., M. V. Dmitriev, A. A. Gorbunov, and V. A. Glushkov. "Complexes of palladium(II) with N-heterocyclic carbenes from adamantylimidazole as precatalysts for thiophene and imidazole arylation." Russian Chemical Bulletin 68, no. 11 (November 2019): 2039–47. http://dx.doi.org/10.1007/s11172-019-2664-3.

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40

Li, Hongfang, Jian Lü, Jingxiang Lin, Yuanbiao Huang, Minna Cao, and Rong Cao. "Crystalline Hybrid Solid Materials of Palladium and Decamethylcucurbit[5]uril as Recoverable Precatalysts for Heck Cross-Coupling Reactions." Chemistry - A European Journal 19, no. 46 (October 7, 2013): 15661–68. http://dx.doi.org/10.1002/chem.201301703.

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41

Li, Liuyi, Jinyun Wang, Chunshan Zhou, Ruihu Wang, and Maochun Hong. "pH-Responsive chelating N-heterocyclic dicarbene palladium(ii) complexes: recoverable precatalysts for Suzuki–Miyaura reaction in pure water." Green Chemistry 13, no. 8 (2011): 2071. http://dx.doi.org/10.1039/c1gc15312a.

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42

John, Alex, Mobin M. Shaikh, Ray J. Butcher, and Prasenjit Ghosh. "Highly efficient palladium precatalysts of homoscorpionate bispyrazolyl ligands for the more challenging Suzuki–Miyaura cross-coupling of aryl chlorides." Dalton Transactions 39, no. 31 (2010): 7353. http://dx.doi.org/10.1039/c003174g.

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43

Baker, Murray V., David H. Brown, Peter V. Simpson, Brian W. Skelton, and Allan H. White. "Synthesis and Characterisation of (Alkoxybenzimidazolin-2-ylidene)palladium Complexes: The Effect of Ancillary Ligands on the Behaviour of Precatalysts." European Journal of Inorganic Chemistry 2009, no. 13 (May 2009): 1977–88. http://dx.doi.org/10.1002/ejic.200801154.

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44

Dash, Chandrakanta, Mobin M. Shaikh, Ray J. Butcher, and Prasenjit Ghosh. "A comparison between nickel and palladium precatalysts of 1,2,4-triazole based N-heterocyclic carbenes in hydroamination of activated olefins." Dalton Transactions 39, no. 10 (2010): 2515. http://dx.doi.org/10.1039/b917892a.

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45

Yang, Jin. "Mixed N-heterocycles/N-heterocyclic carbene palladium(II) allyl complexes as precatalysts for direct arylation of azoles with aryl bromides." Tetrahedron 75, no. 14 (April 2019): 2182–87. http://dx.doi.org/10.1016/j.tet.2019.02.031.

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46

Li, Liuyi, Jinyun Wang, Chunshan Zhou, Ruihu Wang, and Maochun Hong. "ChemInform Abstract: pH-Responsive Chelating N-Heterocyclic Dicarbene Palladium(II) Complexes: Recoverable Precatalysts for Suzuki-Miyaura Reaction in Pure Water." ChemInform 42, no. 51 (November 24, 2011): no. http://dx.doi.org/10.1002/chin.201151076.

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47

Li, Hongfang, Jian Lue, Jingxiang Lin, Yuanbiao Huang, Minna Cao, and Rong Cao. "ChemInform Abstract: Crystalline Hybrid Solid Materials of Palladium and Decamethylcucurbit[5]uril as Recoverable Precatalysts for Heck Cross-Coupling Reactions." ChemInform 45, no. 17 (April 10, 2014): no. http://dx.doi.org/10.1002/chin.201417103.

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48

Cheung, Chi Wai, David S. Surry, and Stephen L. Buchwald. "Mild and Highly Selective Palladium-Catalyzed Monoarylation of Ammonia Enabled by the Use of Bulky Biarylphosphine Ligands and Palladacycle Precatalysts." Organic Letters 15, no. 14 (July 2013): 3734–37. http://dx.doi.org/10.1021/ol401612c.

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49

Lan, Xiao-Bing, Yinwu Li, Yan-Fang Li, Dong-Sheng Shen, Zhuofeng Ke, and Feng-Shou Liu. "Flexible Steric Bulky Bis(Imino)acenaphthene (BIAN)-Supported N-Heterocyclic Carbene Palladium Precatalysts: Catalytic Application in Buchwald–Hartwig Amination in Air." Journal of Organic Chemistry 82, no. 6 (March 6, 2017): 2914–25. http://dx.doi.org/10.1021/acs.joc.6b02867.

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50

Shi, Shicheng, Steven P. Nolan, and Michal Szostak. "Well-Defined Palladium(II)–NHC Precatalysts for Cross-Coupling Reactions of Amides and Esters by Selective N–C/O–C Cleavage." Accounts of Chemical Research 51, no. 10 (September 21, 2018): 2589–99. http://dx.doi.org/10.1021/acs.accounts.8b00410.

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