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Journal articles on the topic 'Palladium-mediated cross-coupling'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Burt, Liam K., Richard L. Cordiner, Anthony F. Hill, Richard A. Manzano, and Jörg Wagler. "The significance of phosphoniocarbynes in halocarbyne cross-coupling reactions." Chemical Communications 56, no. 42 (2020): 5673–76. http://dx.doi.org/10.1039/d0cc02070b.

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Competent intermediates as well as productive and non-productive tangents have been identified in the catalytic cycle for palladium(0)–copper(i) mediated synthesis of propargylidynes via cross coupling reactions of bromocarbyne complexes with alkynes.

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2

Camp, Jason, Thomas Bousfield, Jay Dunsford, et al. "Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions." Synthesis 50, no. 19 (2018): 3862–74. http://dx.doi.org/10.1055/s-0037-1610246.

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A dehydrative cross-coupling of 1-phenylethanol catalysed by sugar derived, in situ formed palladium(0) nanoparticles under acidic conditions is realised. The acidic conditions allow for use of alcohols as a feedstock in metal-mediated coupling reactions via their in situ dehydration and subsequent cross-coupling. Extensive analysis of the size and morphology of the palladium nanoparticles formed in situ showed that the zero-valent metal was surrounded by hydrophilic hydroxyl groups. EDX-TEM imaging studies using a prototype silicon drift detector provided insight into the problematic role of

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3

Sakata, Komei, Daisuke Urabe та Masayuki Inoue. "Preparation and palladium-mediated cross-coupling of α-benzoyloxyalkylzinc bromides". Tetrahedron Letters 54, № 32 (2013): 4189–92. http://dx.doi.org/10.1016/j.tetlet.2013.05.114.

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4

Hillier, Anna C., Gabriela A. Grasa, Mihai S. Viciu, Hon Man Lee, Chuluo Yang, and Steven P. Nolan. "Catalytic cross-coupling reactions mediated by palladium/nucleophilic carbene systems." Journal of Organometallic Chemistry 653, no. 1-2 (2002): 69–82. http://dx.doi.org/10.1016/s0022-328x(02)01154-3.

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5

Grasa, Gabriela A., Mihai S. Viciu, Jinkun Huang, Chunming Zhang, Mark L. Trudell, and Steven P. Nolan. "Suzuki−Miyaura Cross-Coupling Reactions Mediated by Palladium/Imidazolium Salt Systems." Organometallics 21, no. 14 (2002): 2866–73. http://dx.doi.org/10.1021/om020178p.

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6

Indrigo, Eugenio, Jessica Clavadetscher, Sunay V. Chankeshwara, Annamaria Lilienkampf, and Mark Bradley. "Palladium-mediated in situ synthesis of an anticancer agent." Chemical Communications 52, no. 99 (2016): 14212–14. http://dx.doi.org/10.1039/c6cc08666g.

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7

Farina, Vittorio, and Gregory P. Roth. "Catalyst tailoring for palladium-mediated cross coupling of arylstannanes with vinyl triflates." Tetrahedron Letters 32, no. 34 (1991): 4243–46. http://dx.doi.org/10.1016/s0040-4039(00)92138-5.

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8

Hillier, Anna C., Gabriela A. Grasa, Mihai S. Viciu, Hon Man Lee, Chuluo Yang, and Steven P. Nolan. "ChemInform Abstract: Catalytic Cross-Coupling Reactions Mediated by Palladium/Nucleophilic Carbene Systems." ChemInform 33, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.200239248.

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9

Böck, Katharina, Julia E. Feil, Konstantin Karaghiosoff, and Konrad Koszinowski. "Catalyst Activation, Deactivation, and Degradation in Palladium-Mediated Negishi Cross-Coupling Reactions." Chemistry - A European Journal 21, no. 14 (2015): 5548–60. http://dx.doi.org/10.1002/chem.201406408.

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10

Zhao, Zijian, Qiao Zhu, Shiying Che, Zhenghong Luo, and Yan Lian. "Palladium/nickel-mediated cross coupling reaction between phosphorylamides and alkenes toward enephosphorylamides." Synthetic Communications 50, no. 15 (2020): 2338–46. http://dx.doi.org/10.1080/00397911.2020.1774903.

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11

Sakata, Komei, Daisuke Urabe та Masayuki Inoue. "ChemInform Abstract: Preparation and Palladium-Mediated Cross-Coupling of α-Benzoyloxyalkylzinc Bromides." ChemInform 44, № 47 (2013): no. http://dx.doi.org/10.1002/chin.201347046.

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12

Beletskaya, Irina P., and Alexei D. Averin. "New trends in the cross-coupling and other catalytic reactions." Pure and Applied Chemistry 89, no. 10 (2017): 1413–28. http://dx.doi.org/10.1515/pac-2016-1110.

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AbstractA mini-review covers the latest achievements in the field of metal-mediated cross-coupling reactions among which are palladium-catalyzed Heck, Suzuki, cyanation and amination reactions. The aspects of the application of Pd nanoparticles (PdNPs) are discussed. The possibilities of the applications of Cu(I)-catalyzed reactions are described. Special emphasis is made on the synthesis of polymacrocyclic compounds like porphyrin dyads and triads, polyazacryptands bearing fluorophore groups using catalytic methods. The application of Pd-catalyzed CH-activation reactions for porphyrin modific

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13

Dondoni, Alessandro, Marco Fogagnolo, Alessandro Medici, and Elisabeta Negrini. "Palladium-Mediated Cross-Coupling Reactions Between Stannyl- and Bromothiazoles. Preparation of Thiazole Oligomers." Synthesis 1987, no. 02 (1987): 185–86. http://dx.doi.org/10.1055/s-1987-27884.

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14

Zhao, Wenjun, Hong Geun Lee, Stephen L. Buchwald, and Jacob M. Hooker. "Direct 11CN-Labeling of Unprotected Peptides via Palladium-Mediated Sequential Cross-Coupling Reactions." Journal of the American Chemical Society 139, no. 21 (2017): 7152–55. http://dx.doi.org/10.1021/jacs.7b02761.

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15

Lim, Reyna K. V., Nan Li, Carlo P. Ramil, and Qing Lin. "Fast and Sequence-Specific Palladium-Mediated Cross-Coupling Reaction Identified from Phage Display." ACS Chemical Biology 9, no. 9 (2014): 2139–48. http://dx.doi.org/10.1021/cb500443x.

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16

Piber, Michael, Anne Eeg Jensen, Mario Rottländer, and Paul Knochel. "New Efficient Nickel- and Palladium-Catalyzed Cross-Coupling Reactions Mediated by Tetrabutylammonium Iodide." Organic Letters 1, no. 9 (1999): 1323–26. http://dx.doi.org/10.1021/ol9907872.

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17

de Bruijn, A. Dowine, and Gerard Roelfes. "Catalytic Modification of Dehydroalanine in Peptides and Proteins by Palladium-Mediated Cross-Coupling." Chemistry - A European Journal 24, no. 48 (2018): 12728–33. http://dx.doi.org/10.1002/chem.201802846.

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18

Lee, Phil Ho, Dong Seomoon, Kooyeon Lee, et al. "Palladium-Indium-Indium(III) Chloride-Mediated Allyl Cross-Coupling Reactions Using Allyl Acetates." Advanced Synthesis & Catalysis 346, no. 13-15 (2004): 1641–45. http://dx.doi.org/10.1002/adsc.200404125.

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19

Grasa, Gabriela A., Mihai S. Viciu, Jinkun Huang, Chunming Zhang, Mark L. Trudell, and Steven P. Nolan. "ChemInform Abstract: Suzuki-Miyaura Cross-Coupling Reactions Mediated by Palladium/Imidazolium Salt Systems." ChemInform 33, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.200246122.

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20

Odell, Luke, Mats Larhed, and Linda Åkerbladh. "Palladium-Catalyzed Molybdenum Hexacarbonyl-Mediated Gas-Free Carbonylative Reactions." Synlett 30, no. 02 (2018): 141–55. http://dx.doi.org/10.1055/s-0037-1610294.

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This account summarizes Pd(0)-catalyzed Mo(CO)6-mediated gas-free carbonylative reactions published in the period October 2011 to May 2018. Presented reactions include inter- and intramolecular carbonylations, carbonylative cross-couplings, and carbonylative multicomponent reactions using Mo(CO)6 as a solid source of CO. The presented methodologies were developed mainly for small-scale applications, avoiding the problematic use of gaseous CO in a standard laboratory. In most cases, the reported Mo(CO)6-mediated carbonylations were conducted in sealed vials or by using two-chamber solutions.1 I

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21

Kaliyaperumal, Srinivasan A., Shyamapada Banerjee, and Syam Kumar U. K. "Palladium mediated intramolecular multiple C–X/C–H cross coupling and C–H activation: synthesis of carbazole alkaloids calothrixin B and murrayaquinone A." Org. Biomol. Chem. 12, no. 32 (2014): 6105–13. http://dx.doi.org/10.1039/c4ob00493k.

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22

Xie, Pan, Cheng Xue, Cancan Wang, Dongdong Du, and SanShan Shi. "Merging CF3SO2Na photocatalysis with palladium catalysis to enable decarboxylative cross-coupling for the synthesis of aromatic ketones at room temperature." Organic Chemistry Frontiers 8, no. 13 (2021): 3427–33. http://dx.doi.org/10.1039/d1qo00438g.

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By merging CF<sub>3</sub>SO<sub>2</sub>Na-mediated photocatalysis with palladium catalysis, an efficient decarboxylative coupling strategy of α-keto acids and aryl boronic acids has been developed for the synthesis of aromatic ketones.

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23

Besev, Magnus, Christof Brehm, and Alois Fürstner. "Formal Total Syntheses of Crocacin A-D." Collection of Czechoslovak Chemical Communications 70, no. 10 (2005): 1696–708. http://dx.doi.org/10.1135/cccc20051696.

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A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

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24

Jennings, Michael P., Elizabeth A. Cork, and P. Veeraraghavan Ramachandran. "A Facile Synthesis of Perfluoroalkyl Vinyl Iodides and Their Palladium-Mediated Cross-Coupling Reactions1." Journal of Organic Chemistry 65, no. 25 (2000): 8763–66. http://dx.doi.org/10.1021/jo001318c.

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25

Gordon, Richard S., and Andrew B. Holmes. "ChemInform Abstract: Palladium-Mediated Cross-Coupling Reactions with Supported Reagents in Supercritical Carbon Dioxide." ChemInform 33, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.200229078.

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26

FARINA, V., and G. P. ROTH. "ChemInform Abstract: Catalyst Tailoring for Palladium-Mediated Cross Coupling of Arylstannanes with Vinyl Triflates." ChemInform 23, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199220097.

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27

Chen, Han, and Min-Zhi Deng. "Silver Oxide Mediated Palladium-Catalyzed Cross-Coupling Reaction of Cyclopropylboronic Acids with Allylic Bromides." Journal of Organic Chemistry 65, no. 14 (2000): 4444–46. http://dx.doi.org/10.1021/jo0000933.

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28

Armitage, Mark A., David C. Lathbury, and Joe B. Sweeney. "Preparation of 2-aryl and 2-heteroaryl substituted penems by palladium mediated cross coupling." Tetrahedron Letters 36, no. 5 (1995): 775–76. http://dx.doi.org/10.1016/0040-4039(94)02365-i.

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29

Banwell, MG, JM Cameron, MP Collis, et al. "The Palladium-Mediated Cross Coupling of Bromotropolones With Organostannanes or Arylboronic Acids: Applications to the Synthesis of Natural Products and Natural Product Analogs." Australian Journal of Chemistry 44, no. 5 (1991): 705. http://dx.doi.org/10.1071/ch9910705.

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The bromotropolones (4), (5) and (10) undergo palladium-mediated cross coupling with a wide range of organostannanes to produce alkenyl -, alkyl- and aryl-substituted tropolones . The methodology has been applied to the synthesis of the monoterpenes β- dolabrin (11),β- thujaplicin (12), 4-isopropyl-7-methoxytropolone (13) and β- thujaplicinol (14). Cross coupling of bromotropolones (4), (5) and (10) with various aryltrimethylstannanes or arylboronic acids has permitted the preparation of the bicyclic colchicine analogues (30)-(43) which have been tested for tubulin -binding activity. The X-ray

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30

Palát, Karel, and Malcolm F. G. Stevens. "Structural studies on bioactive compounds. Part 33. Synthesis of 9-arylacridines by palladium-mediated couplings." Journal of Chemical Research 2000, no. 3 (2000): 136–37. http://dx.doi.org/10.3184/030823400103166698.

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31

Iwao, Masatomo, Hirokazu Takehara, Sunao Furukawa, and Mitsuaki Watanabe. "A Regiospecific Synthesis of Carbazoles via Consecutive Palladium-catalyzed Cross-coupling and Aryne-mediated Cyclization." HETEROCYCLES 36, no. 7 (1993): 1483. http://dx.doi.org/10.3987/com-93-6368.

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32

Hatanaka, Yasuo, Koji Matsui, and Tamejiro Hiyama. "A one-pot synthesis of conjugated dienynes by palladium-mediated three component cross-coupling reaction." Tetrahedron Letters 30, no. 18 (1989): 2403–6. http://dx.doi.org/10.1016/s0040-4039(01)80411-1.

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33

Kazzouli, Saïd El, Latifa Bouissane, Mostafa Khouili, and Gérald Guillaumet. "Synthesis of 4-substituted and 3,4-disubstituted indazole derivatives by palladium-mediated cross-coupling reactions." Tetrahedron Letters 46, no. 36 (2005): 6163–67. http://dx.doi.org/10.1016/j.tetlet.2005.06.080.

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34

Shu, Chutian, Kanwar Sidhu, Li Zhang, Xiao-jun Wang, Dhileepkumar Krishnamurthy, and Chris H. Senanayake. "Palladium-Catalyzed Cross-Coupling of Cyclopropylmagnesium Bromide with Aryl Bromides Mediated by Zinc Halide Additives." Journal of Organic Chemistry 75, no. 19 (2010): 6677–80. http://dx.doi.org/10.1021/jo100983c.

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35

Piber, Michael, Anne Eeg Jensen, Mario Rottlaender, and Paul Knochel. "ChemInform Abstract: New Efficient Nickel- and Palladium-Catalyzed Cross-Coupling Reactions Mediated by Tetrabutylammonium Iodide." ChemInform 31, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.200004076.

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36

Bennett, Jeffrey A., Andrew J. Kristof, Vishal Vasudevan, Jan Genzer, Jiri Srogl, and Milad Abolhasani. "Microfluidic synthesis of elastomeric microparticles: A case study in catalysis of palladium-mediated cross-coupling." AIChE Journal 64, no. 8 (2018): 3188–97. http://dx.doi.org/10.1002/aic.16119.

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37

Wuest, Frank R., and Mathias Berndt. "11C–C bond formation by palladium-mediated cross-coupling of alkenylzirconocenes with [11C]methyl iodide." Journal of Labelled Compounds and Radiopharmaceuticals 49, no. 2 (2006): 91–100. http://dx.doi.org/10.1002/jlcr.1044.

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38

Han, Xiaodong, Zhizhou Yue, Xiaofei Zhang, Qian He, and Chunhao Yang. "Copper-Mediated, Palladium-Catalyzed Cross-Coupling of 3-Iodochromones, Thiochromones, and Quinolones with Ethyl Bromodifluoroacetate." Journal of Organic Chemistry 78, no. 10 (2013): 4850–56. http://dx.doi.org/10.1021/jo400412k.

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39

Arasavelli, Ananda Mohan, Ganapavarapu Veera Raghava Sharma, and Siddaiah Vidavalur. "Design, synthesis, and anticancer activity of novel aryl/heteroaryl chalcone derivatives." Heterocyclic Communications 22, no. 1 (2016): 1–5. http://dx.doi.org/10.1515/hc-2015-0271.

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AbstractA new series of chalcones 5a–l were synthesized and evaluated for in vitro antiproliferative activity against human colon cancer cell lines. The synthesis of the key intermediate compounds 3a–d was achieved by tetrakis(triphenylphosphine) palladium(II) mediated Suzuki cross coupling reaction. Chalcone 5a shows superior anticancer activity with IC50 value of 21.0 μg/mL compared to the IC50 value of the reference drug doxorubicin at 21.65 μg/mL.

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40

Lu, Hai-Long, Fu-Hu Guo, Tong-Lin Wang, Xi-Cun Wang, and Zheng-Jun Quan. "Palladium-Catalyzed/Copper-Mediated Desulfurization and Arylation of Quinoline-2-(1H)-thione for Rapid Access to Quinoline Derivatives." Synthesis 52, no. 06 (2019): 893–900. http://dx.doi.org/10.1055/s-0039-1690765.

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An efficient method for carbon–carbon bond formation is described. The process employs the palladium-catalyzed and copper-mediated cross-coupling of quinoline-2-(1H)-thiones with arylboronic acids or alkynes through C–S bond cleavage without an inert atmosphere. The method provides rapid and general access to a diverse range of 2-substituted quinolines in a single step from a wide range of quinoline-2-(1H)-thiones and arylboronic acids or alkynes.

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41

Mphahlele, Malose J., and Temitope O. Olomola. "Synthesis and Transformation of 5-Acetyl-2-aryl-6-hydroxybenzofurans into Furanoflavanone Derivatives." Synthesis 51, no. 18 (2019): 3431–42. http://dx.doi.org/10.1055/s-0039-1690001.

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Tandem palladium-catalyzed Sonogashira cross-coupling and heteroannulation of 3-bromo-2,4-dihydroxy-5-iodoacetophenone with arylacetylenes followed by the base-mediated Claisen–Schmidt aldol condensation of the intermediate 5-acetyl-2-aryl-7-bromo-6-hydroxybenzofurans with benzaldehyde derivatives afforded the corresponding linear 2-arylbenzofuranchalcone hybrids. The presence of the o-hydroxy-trans-α,β-unsaturated carbonyl moiety in the prepared furanochalcone hybrids facilitated acid-mediated cycloisomerization into the corresponding linear furanoflavanones. The structures of the prepared co

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42

Merner, Bradley, Nirmal Mitra, and Caroline Merryman. "Highly Strained para-Phenylene-Bridged Macrocycles from Unstrained 1,4-Diketo Macrocycles." Synlett 28, no. 17 (2017): 2205–11. http://dx.doi.org/10.1055/s-0036-1589081.

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The conversion of macrocyclic 1,4-diketones to highly strained para-phenylene rings has recently been reported by our laboratory. This synthetic strategy represents a non-cross-coupling-based approach to arene-bridged macrocycles, and an alternative to palladium- and nickel-mediated processes. In this Synpacts article we discuss the development of endgame aromatization protocols for the synthesis of increasingly strained arene systems, as well as potential advantages of the macrocyclic 1,4-diketone approach to selectively functionalized benzenoid macrocycles for future complexity building reac

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43

Tezuka, Yasuyuki, Ryota Komiya, Yoshito Ido, and Kaoru Adachi. "Synthesis and palladium-mediated cross-coupling reaction of cyclic (kyklo-) and open-chain (kentro-) telechelic precursors." Reactive and Functional Polymers 67, no. 11 (2007): 1233–42. http://dx.doi.org/10.1016/j.reactfunctpolym.2007.06.013.

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44

Atmuri, N. "Preparation of N-(Boc)-Allylglycine Methyl Ester Using a Zinc-mediated, Palladium-catalyzed Cross-coupling Reaction." Organic Syntheses 92 (2015): 103–16. http://dx.doi.org/10.15227/orgsyn.092.0103.

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45

Hatanaka, Yasuo, and Tamejiro Hiyama. "Highly Selective Cross-Coupling Reactions of Organosilicon Compounds Mediated by Fluoride Ion and a Palladium Catalyst." Synlett 1991, no. 12 (1991): 845–53. http://dx.doi.org/10.1055/s-1991-20899.

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46

Jennings, Michael P., Elizabeth A. Cork, and P. Veeraraghavan Ramachandran. "ChemInform Abstract: A Facile Synthesis of Perfluoroalkyl Vinyl Iodides and Their Palladium-Mediated Cross-Coupling Reactions." ChemInform 32, no. 17 (2001): no. http://dx.doi.org/10.1002/chin.200117078.

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47

Chen, Han, and Min-Zhi Deng. "ChemInform Abstract: Silver Oxide Mediated Palladium-Catalyzed Cross-Coupling Reaction of Cyclopropylboronic Acids with Allylic Bromides." ChemInform 31, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.200046084.

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48

Yanada, Reiko, Shingo Obika, Yusuke Kobayashi, et al. "Stereoselective Synthesis of 3-Alkylideneoxindoles using Tandem Indium-Mediated Carbometallation and Palladium-Catalyzed Cross-Coupling Reactions." Advanced Synthesis & Catalysis 347, no. 11-13 (2005): 1632–42. http://dx.doi.org/10.1002/adsc.200505147.

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49

ARMITAGE, M. A., D. C. LATHBURY, and J. B. SWEENEY. "ChemInform Abstract: Preparation of 2-Aryl- and 2-Heteroaryl-Substituted Penems by Palladium-Mediated Cross Coupling." ChemInform 26, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199523244.

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50

Savarin, Cecile, Jiri Srogl, and Lanny S. Liebeskind. "Substituted Alkyne Synthesis under Nonbasic Conditions: Copper Carboxylate-Mediated, Palladium-Catalyzed Thioalkyne−Boronic Acid Cross-Coupling." Organic Letters 3, no. 1 (2001): 91–93. http://dx.doi.org/10.1021/ol006807d.

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