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Journal articles on the topic 'Heck reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Kurandina, Daria, Padon Chuentragool, and Vladimir Gevorgyan. "Transition-Metal-Catalyzed Alkyl Heck-Type Reactions." Synthesis 51, no. 05 (2019): 985–1005. http://dx.doi.org/10.1055/s-0037-1611659.

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The Heck reaction is one of the most reliable and useful strategies for the construction of C–C bonds in organic synthesis. However, in contrast to the well-established aryl Heck reaction, the analogous reaction employing alkyl electrophiles is much less developed. Significant progress in this area was recently achieved by merging radical-mediated and transition-metal-catalyzed approaches. This review summarizes the advances in alkyl Heck-type reactions from its discovery early in the 1970s up until the end of 2018.1 Introduction2 Pd-Catalyzed Heck-Type Reactions2.1 Benzylic Electrophiles2.2 α

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2

Newman, Stephen, and Jaya Vandavasi. "A High-Throughput Approach to Discovery: Heck-Type Reactivity with Aldehydes." Synlett 29, no. 16 (2018): 2081–86. http://dx.doi.org/10.1055/s-0037-1610161.

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The classical Heck reaction is among the most powerful methods available for the construction of C–C bonds. Modification of this transformation to utilize diverse organohalide coupling partners has resulted in new reactions such as the silyl-Heck, aza-Heck, and boryl-Heck reactions. In contrast, modification of the olefin coupling partner is rare. For instance, use of the π-bond of an aldehyde instead of an alkene would provide ketones via a carbonyl-Heck process. This seemingly minor manipulation of the Heck reaction has proven surprisingly difficult to realize in practice. Through the use of

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3

Wall, Valerie M., Amihai Eisenstadt, David J. Ager, and Scott A. Laneman. "The Heck Reaction and Cinnamic Acid Synthesis by Heterogeneous Catalysis." Platinum Metals Review 43, no. 4 (1999): 138–45. http://dx.doi.org/10.1595/003214099x434138145.

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The Heck reaction for the construction of carbon-carbon bonds, using palladium catalysts, is one of the most valuable strategies in organic chemistry and appears frequently in the literature, usually as homogeneous catalysis. In this review the progress made to date with this reaction is examined, together with the most discussed aspects of the Heck reaction, including a description of its mechanism and the conditions required for success. Some limitations to the homogeneous reaction are mentioned with reasons for proceeding with heterogeneous catalysts, in particular with palladium/carbon. Ex

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4

Lee, Jin-Kyun, Rachel M. Williamson, Andrew B. Holmes, Edward J. Bush, and Ian F. McConvey. "A Study of the Heck Reaction in Non-Polar Hydrocarbon Solvents and in Supercritical Carbon Dioxide." Australian Journal of Chemistry 60, no. 8 (2007): 566. http://dx.doi.org/10.1071/ch07160.

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The effects of electronic and steric properties of phosphorus ligands on Heck reactions in supercritical CO2 and non-polar hydrocarbon solvents were studied. In Heck reactions between iodobenzene and butyl acrylate, higher yields were obtained with less electron-rich phosphine ligands. This trend was also observed with the electron-poor triphenyl phosphite. A range of sterically demanding phosphites were then investigated. Biphenyl-containing phosphites 8 and 13 were found to be highly effective. In the Heck reaction between the less-reactive bromobenzene and butyl acrylate, the bulky, electro

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5

Díaz-Ortiz, Ángel, Pilar Prieto, Abel de Cózar, Cristina Cebrián, Andrés Moreno, and Antonio de la Hoz. "Microwave-Controlled Preparation of Alkenyl-(1H)-1,2,4-triazoles: First Heck Reaction on a (1H)-1,2,4-Triazole Moiety." Australian Journal of Chemistry 62, no. 12 (2009): 1600. http://dx.doi.org/10.1071/ch09185.

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A new synthetic approach for the preparation of alkenyl-1,2,4-triazole derivatives based on microwave-induced C–C cross-coupling Heck reactions is described. To the best of our knowledge, this is the first application of the Heck reaction to a dihalogenated 1,2,4-triazole. This approach allows the introduction of a wide range of equivalent or different alkenyl substituents in the 5- and/or 3-positions, thus extending the possibilities for the preparation of these valuable derivatives. A similar microwave-induced synthetic procedure has also been applied to the Heck reaction of 4-vinyl-1,2,3-tr

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6

Shibasaki, Masakatsu, Erasmus M Vogl, and Takashi Ohshima. "Asymmetric Heck Reaction." Advanced Synthesis & Catalysis 346, no. 13-15 (2004): 1533–52. http://dx.doi.org/10.1002/adsc.200404203.

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7

Demidoff, Felipe, Fabrícia de Souza, and Chaquip Netto. "Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400." Synthesis 49, no. 23 (2017): 5217–23. http://dx.doi.org/10.1055/s-0036-1589095.

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Styrenes were coupled with 3-iodolawsone in PEG-400 at 90 °C, leading stereoselectively to (E)-stilbene-quinone hybrids through Heck reactions. The best reaction conditions were found to be the use of NaOH (3 equiv) and 10 mol% of palladium acetate at 90 °C for 15 minutes. The chemical yields of the Heck reactions using styrenes with electron-withdrawing groups (65–98%) were greater than styrenes bearing electron-donating groups (7–32%) on the aromatic ring. In particular, the chemical yields of Heck reactions involving nitrostyrenes were the best ones observed.

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8

Tietze, Lutz F., Lars P. Lücke, Felix Major, and Peter Müller. "Efficient Synthesis of an Enantiopure Thiasteroid by a Double Heck Reaction." Australian Journal of Chemistry 57, no. 7 (2004): 635. http://dx.doi.org/10.1071/ch04034.

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The thiaestrane 7 was synthesized by two sequential Heck reactions starting from the thiophene derivatives 8a–8c, which contain a (Z)-halogenovinyl group, and the enantiopure hydrindene 2a. The first intermolecular Pd-catalyzed reaction leads to 11a and 11b in a highly regio- and diastereoselective manner. A subsequent intramolecular Heck reaction catalyzed by the palladacycle 4 then gave the thiasteroid 7 with an unusual cis-junction of the rings B and C.

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9

de Vries, Johannes G. "The Heck reaction in the production of fine chemicals." Canadian Journal of Chemistry 79, no. 5-6 (2001): 1086–92. http://dx.doi.org/10.1139/v01-033.

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An overview is given of the use of the Heck reaction for the production of fine chemicals. Five commercial products have been identified that are produced on a scale in excess of 1 ton/year. The herbicide Prosulfuron(tm) is produced via a Matsuda reaction of 2-sulfonatobenzenediazonium on 3,3,3-trifluoropropene. The sunscreen agent 2-ethylhexyl p-methoxy-cinnamate has been produced on pilot scale using Pd/C as catalyst. Naproxen(tm) is produced via the Heck reaction of 2-bromo-6-methoxy-naphthalene on ethylene, followed by carbonylation of the product. Monomers for coatings are produced via a

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10

Srivastava, Vivek. "Synthesis and Characterization of Pd exchanged MMT Clay for Mizoroki-Heck Reaction." Open Chemistry 16, no. 1 (2018): 605–13. http://dx.doi.org/10.1515/chem-2018-0065.

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AbstractWe successfully synthesized Pd@MMT clay using a cation exchange process. We characterized all the synthesized Pd@MMT clays using sophisticated analytical techniques before testing them as a heterogeneous catalyst for the Mizoroki - Heck reaction (mono and double). The highest yield of the Mizoroki-Heck reaction product was recovered using thermally stable and highly reactive Pd@ MMT-1 clay catalyst in the functionalized ionic liquid reaction medium. We successfully isolated 2-aryl-vinyl phosphonates (mono-Mizoroki-Heck reaction product) and 2,2-diaryl-vinylphosphonates (double-Mizoroki

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11

Lautens, Mark, and Valentin Zunic. "Sequential olefin metathesis Intramolecular asymmetric Heck reactions in the synthesis of polycycles." Canadian Journal of Chemistry 82, no. 2 (2004): 399–407. http://dx.doi.org/10.1139/v03-196.

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Application of the intramolecular asymmetric Heck reaction in the desymmetrization of a novel class of symmetrical bicyclodienes, synthesized through a diastereoselective double ring-closing metathesis (DSRCM) reaction, was achieved with good yields (approximately 80%) and excellent enantioselectivities (up to 99% ee). Three contiguous stereocenters are established in a single desymmetrization reaction. The use of thallium carbonate as base in the asymmetric Heck reaction favours double bond migration in 13. Cationic conditions delivered products with good to excellent enantioselectivities, su

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12

Shi, Wei, Jingbo Yu, Zhijiang Jiang, Qiaoling Shao, and Weike Su. "Encaging palladium(0) in layered double hydroxide: A sustainable catalyst for solvent-free and ligand-free Heck reaction in a ball mill." Beilstein Journal of Organic Chemistry 13 (August 14, 2017): 1661–68. http://dx.doi.org/10.3762/bjoc.13.160.

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In this paper, the synthesis of a cheap, reusable and ligand-free Pd catalyst supported on MgAl layered double hydroxides (Pd/MgAl-LDHs) by co-precipitation and reduction methods is described. The catalyst was used in Heck reactions under high-speed ball milling (HSBM) conditions at room temperature. The effects of milling-ball size, milling-ball filling degree, reaction time, rotation speed and grinding auxiliary category, which would influence the yields of mechanochemical Heck reactions, were investigated in detail. The characterization results of XRD, ICP–MS and XPS suggest that Pd/MgAl-LD

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13

Wang, Sa-Sa, and Guo-Yu Yang. "Recent developments in low-cost TM-catalyzed Heck-type reactions (TM = transition metal, Ni, Co, Cu, and Fe)." Catalysis Science & Technology 6, no. 9 (2016): 2862–76. http://dx.doi.org/10.1039/c5cy02235e.

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14

Lee, A. L. "Enantioselective oxidative boron Heck reactions." Organic & Biomolecular Chemistry 14, no. 24 (2016): 5357–66. http://dx.doi.org/10.1039/c5ob01984b.

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15

Reddy, K. Sateesh, Bandi Siva, S. Divya Reddy, et al. "In Situ FTIR Spectroscopic Monitoring of the Formation of the Arene Diazonium Salts and Its Applications to the Heck–Matsuda Reaction." Molecules 25, no. 9 (2020): 2199. http://dx.doi.org/10.3390/molecules25092199.

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This study depicts the use of a fiber-optic coupled Fourier transform infrared spectroscopy-attenuated total reflection (FTIR-ATR) probe for the in-depth study of arene diazonium salt formation and their utilization in the Heck–Matsuda reaction. The combination of these chemical reactions and in situ IR spectroscopy enabled us to recognize the optimum parameters for arene diazonium salt formation and to track the concentrations of reactants, products and intermediates under actual reaction conditions without time consuming HPLC analysis and the necessity of collecting the sample amid the react

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16

García, Carolina S., Paula M. Uberman, and Sandra E. Martín. "An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation." Beilstein Journal of Organic Chemistry 13 (August 18, 2017): 1717–27. http://dx.doi.org/10.3762/bjoc.13.166.

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Aqueous Mizoroki–Heck coupling reactions under microwave irradiation (MW) were carried out with a colloidal Pd nanocatalyst stabilized with poly(N-vinylpyrrolidone) (PVP). Many stilbenes and novel heterostilbenes were achieved in good to excellent yields starting from aryl bromides and different olefins. The reaction was carried out in a short reaction time and with low catalyst loading, leading to high turnover frequency (TOFs of the order of 100 h−1). The advantages like operational simplicity, high robustness, efficiency and turnover frequency, the utilization of aqueous media and simple pr

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17

Le Bras, Jean, and Jacques Muzart. "Pd-Catalyzed Intermolecular Dehydrogenative Heck Reactions of Five-Membered Heteroarenes." Catalysts 10, no. 5 (2020): 571. http://dx.doi.org/10.3390/catal10050571.

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The Pd-mediated cross-coupling of (hetero)arenes with alkenes may be an effective method for the formation of a C–C bond from two C–H bonds. Discovered by Fujiwara and co-workers in 1967, this reaction led to a number of reports that we firstly highlighted in 2011 (review with references till June 2010) and for which, we retained the name “dehydrogenative Heck reaction”. The topic, especially the reactions of five-membered heteroarenes, has been the subject of intensive research over the last ten years. The present review is limited to these dehydrogenative Heck reactions published since 2010,

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18

Signori, Aline M., Eloah Latocheski, Brunno L. Albuquerque, et al. "Aqueous intramolecular Mizoroki–Heck reaction of (2-iodophenyl)(3-methyl-1H-indol-1-yl)methanone: a model reaction for the in situ performance evaluation of Pd catalysts." New Journal of Chemistry 39, no. 3 (2015): 1574–78. http://dx.doi.org/10.1039/c4nj01921k.

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19

Schmidt, Bernd. "The Mizoroki-Heck Reaction." Synthesis 2010, no. 04 (2010): 718. http://dx.doi.org/10.1055/s-0029-1218660.

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20

Shibasaki, Masakatsu, Christopher D. J. Boden, and Akihiko Kojima. "The asymmetric Heck reaction." Tetrahedron 53, no. 22 (1997): 7371–95. http://dx.doi.org/10.1016/s0040-4020(97)00437-7.

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21

Mayasundari, Anand, and David G. J. Young. "Silicon-tethered Heck reaction." Tetrahedron Letters 42, no. 2 (2001): 203–6. http://dx.doi.org/10.1016/s0040-4039(00)01910-9.

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22

Gibson (née Thomas), Susan E., and Richard J. Middleton. "The intramolecular Heck reaction." Contemp. Org. Synth. 3, no. 6 (1996): 447–71. http://dx.doi.org/10.1039/co9960300447.

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23

Shibasaki, Masakatsu, and Erasmus M. Vogl. "ChemInform Abstract: Heck Reaction." ChemInform 31, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.200018245.

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24

Mittal, Kavita, and Pragya Gahlot. "Nickel-Catalyzed Heck Reaction." SynOpen 07, no. 01 (2023): 114–16. http://dx.doi.org/10.1055/s-0042-1751432.

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25

Gupta, Sumanta, Bhaskar Ganguly, and Sajal Das. "A straight forward synthesis of 4-aryl substituted 2-quinolones via Heck reaction." RSC Adv. 4, no. 77 (2014): 41148–51. http://dx.doi.org/10.1039/c4ra06284a.

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Pd–NHC catalyzed one pot synthesis of 4-aryl-2-quinolones through the Heck reaction followed by cyclization. Additionally an efficient methodology has been developed for Heck reaction with a wide range of arylhalides and olefins.

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26

Jadhav, Sanjay N., Arjun S. Kumbhar, Chadrashekhar V. Rode, and Rajashri S. Salunkhe. "Ligand-free Pd catalyzed cross-coupling reactions in an aqueous hydrotropic medium." Green Chemistry 18, no. 7 (2016): 1898–911. http://dx.doi.org/10.1039/c5gc02314a.

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A simple, efficient and ligand-free protocol for the Suzuki–Miyaura reaction and base-free Heck–Matsuda reactions under mild reaction conditions has been developed over palladium supported on activated carbon (Pd/C) in an aqueous hydrotropic solution.

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27

Kostyukovich, A. Yu, E. D. Patil, J. V. Burykina, and V. P. Ananikov. "Transformations of Pd/(N-Heterocyclic Carbene) Molecular Complexes into a Nanosized Catalytic Systems in the Mizoroki–Heck Reaction." Кинетика и катализ 64, no. 1 (2023): 53–64. http://dx.doi.org/10.31857/s0453881123010033.

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The mechanism of the formation of catalytic species in the practically important Mizoroki–Heck reaction, which is in demand in modern fine organic synthesis, has been studied. It has been shown that catalysts based on palladium complexes with N-heterocyclic carbene ligands are transformed into a “ligand-free” form under the conditions of the Mizoroki–Heck reaction. Molecular modeling performed using quantum chemical methods showed that these processes compete with the target reaction at three of the six stages of the catalytic cycle. The presence of catalyst transformation products in the reac

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28

Zhu, Xiaoyan, Feng Liu, Xinwu Ba, and Yonggang Wu. "Tandem Suzuki Polymerization/Heck Cyclization Reaction to Form Ladder-Type 9,9′-Bifluorenylidene-Based Conjugated Polymer." Polymers 15, no. 16 (2023): 3360. http://dx.doi.org/10.3390/polym15163360.

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The synthesis of ladder-type 9,9′-bifluorenylidene-based conjugated polymer is reported. Unlike the typical synthetic strategy, the new designed ladder-type conjugated polymer is achieved via tandem Suzuki polymerization/Heck cyclization reaction in one-pot. In the preparation process, Suzuki polymerization reaction occurred first and then the intramolecular Heck cyclization followed smoothly under the same catalyst Pd(PPh3)4. The model reaction proved that the introduction of iodine (I) for this tandem reaction can effectively control the sequential bond-forming process and inhibit the additi

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29

Hajipour, Abdol R., Parisa Abolfathi, and Fatemeh Mohammadsaleh. "A click strategy for the immobilization of palladium nanoparticles onto silica: efficient and recyclable catalysts for carbon–carbon bond formation under mild reaction conditions." RSC Advances 6, no. 81 (2016): 78080–89. http://dx.doi.org/10.1039/c6ra11734a.

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30

Putta, Chandrababu, Vittal Sharavath, Suprabhat Sarkar та Sutapa Ghosh. "Palladium nanoparticles on β-cyclodextrin functionalised graphene nanosheets: a supramolecular based heterogeneous catalyst for C–C coupling reactions under green reaction conditions". RSC Advances 5, № 9 (2015): 6652–60. http://dx.doi.org/10.1039/c4ra14323j.

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Palladium nanoparticles on β-cyclodextrin functionalised graphene based supramolecular heterogeneous catalyst are used for Suzuki–Miyaura and Heck–Mizoroki coupling reactions under green reaction conditions.

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31

Chen, Chen, Wan Sun, Liying Liu, et al. "Palladium-catalyzed domino Heck-disilylation and Heck-monosilylation of alkene-tethered carbamoyl chlorides: synthesis of versatile silylated oxindoles." Organic Chemistry Frontiers 8, no. 10 (2021): 2250–55. http://dx.doi.org/10.1039/d1qo00221j.

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32

Sarkar, Shaheen M., Md Lutfor Rahman, and Mashitah Mohd Yusoff. "Heck, Suzuki and Sonogashira cross-coupling reactions using ppm level of SBA-16 supported Pd-complex." New Journal of Chemistry 39, no. 5 (2015): 3564–70. http://dx.doi.org/10.1039/c4nj02319f.

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33

Shults, E. E. "Modification of Biologically Active Plant Metabolites Via the Transition Metal Catalyzed Reactions." Eurasian Chemico-Technological Journal 15, no. 3 (2013): 175. http://dx.doi.org/10.18321/ectj221.

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Developed by the author’s research laboratory methods of functionalization of some plant metabolites or their derivatives, viz., the eudesmane-type methylenelactones, diterpene and morphinane alkaloids, furanolabdanoids, and coumarins, using the transition metal catalyzed reactions, are reviewed. The activity<br />of linear methylene lactone of the eudesmane type in the Heck reaction are analyzed. It is shown that the outcome of the Heck reaction is significantly influenced by the structure of methylidenelactone. The Pd-catalyzed arylation of isoalantolactone with arylhalogenides or 6-br

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34

Xu, Qijie, Wenzhong Shi, and Yuanchen Cui. "Synthesis of the cross-linked humic acid supporting palladium catalyst and its catalytic properties for Heck reaction." Polish Journal of Chemical Technology 14, no. 2 (2012): 75–79. http://dx.doi.org/10.2478/v10026-012-0074-5.

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Synthesis of the cross-linked humic acid supporting palladium catalyst and its catalytic properties for Heck reaction Cross-linked humic acid supporting palladium (CL-HA-Pd) catalyst was prepared readily and characterized by infrared analysis (IR) and thermogravimetric analysis (TG). The catalyst could catalyze the Heck reaction of aryl halide or substituted aryl halide with vinyl compounds in N2 atmosphere; the yields were above 95%. The catalyst could be recovered and reused 7 times with the Heck reaction of iodobenzene with acrylic acid, and the yield was above 75.6%. The results showed tha

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35

Shu, Xing-Zhong, Xiaobo Pang, and Xuejing Peng. "Reductive Cross-Coupling of Vinyl Electrophiles." Synthesis 52, no. 24 (2020): 3751–63. http://dx.doi.org/10.1055/s-0040-1707342.

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The synthesis of alkenes (olefins) is a central subject in the synthetic community. The transition-metal-catalyzed reductive cross-coupling of vinyl electrophiles has emerged as a promising tool to produce alkenes with improved flexibility, structural complexity, and functionality tolerance. In this review, we summarized the progress in this field with respect to cross-electrophile couplings and reductive Heck reactions using vinyl electrophiles.1 Introduction2 Cross-Electrophile Coupling of Vinyl Electrophiles3 Reductive Heck Reaction of Vinyl Electrophiles4 Summary and Outlook

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36

Lim, Li Hui, and Jianrong (Steve) Zhou. "A challenging Heck reaction of maleimides." Organic Chemistry Frontiers 2, no. 7 (2015): 775–77. http://dx.doi.org/10.1039/c5qo00015g.

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37

Zhang, Yan Hua, E. Yu Ji, Song Tao Chen, and Da Min Tian. "Ligand-Free and Regioselectivity of the Heck Reaction Catalyzed by Pd(0) Nanoparticles at Ambient Conditions under Ultrasonic Irradiation." Advanced Materials Research 113-116 (June 2010): 1675–78. http://dx.doi.org/10.4028/www.scientific.net/amr.113-116.1675.

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The Heck reaction proceeded in isopropanol under ultrasonic irradiation at ambient temperature (30°C) has been reported in this report. The Heck reaction showed excellent regio- selectivity, enhanced reaction rates, high yields, and the conditions were mild and environmentally friendly. It was found that as a heterogeneous catalyst for the reaction palladium forms nano- particles in-situ, and can be recycled for many times. Transmission electron microscopy (TEM) and X-ray powder diffraction (XRD) analysis characteried the formation of stable, crystalline Pd(0) nanoparticles as catalyst for the

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38

Jin, Tony, Malickah Hicks, Davis Kurdyla, Sabahudin Hrapovic, Edmond Lam, and Audrey Moores. "Palladium nanoparticles supported on chitin-based nanomaterials as heterogeneous catalysts for the Heck coupling reaction." Beilstein Journal of Organic Chemistry 16 (October 7, 2020): 2477–83. http://dx.doi.org/10.3762/bjoc.16.201.

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In this report, chitin and chitosan nanocrystals were used as biomass-based supports for Pd nanoparticles (NPs) used as a heterogeneous catalyst for the Heck coupling reaction. By using a one-pot fabrication method, a Pd salt precursor was directly reduced and deposited onto these nanocrystal catalysts. Characterization of these nanocomposites showed disperse Pd NPs on the surfaces of the chitinous nanocrystals. Heck coupling model reactions revealed full product yield in relatively benign conditions, outcompeting the use of other catalysts supported on biomass-based nanomaterials, including c

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39

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

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(±)-2,2′-Bis(diphenylphosphino)-3,3′-binaphtho[2,1-b]furan (BINAPFu) was synthesized from 2-naphthoxyacetic acid in a five-step sequence in 62% overall yield. A variety of reported resolution procedures for biaryl bisphosphines did not work with (±)-BINAPFu; thus, a new resolution method was developed, involving the Staudinger reaction of the aforementioned racemate of BINAPFu with an enantiopure camphor sulfonyl azide derivative. The resulting diastereomeric phosphinimines were separated by flash chromatography. Subsequent hydrolysis to the corresponding bis-phosphine oxide and trichlorosilan

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40

Bhilare, Shatrughn, Vijay Gayakhe, Ajaykumar V. Ardhapure, et al. "Novel water-soluble phosphatriazenes: versatile ligands for Suzuki–Miyaura, Sonogashira and Heck reactions of nucleosides." RSC Advances 6, no. 87 (2016): 83820–30. http://dx.doi.org/10.1039/c6ra19039a.

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Two new water-soluble phosphatriazene as versatile ligands for catalyzing Suzuki–Miyaura reactions of purines and pyrimidines in neat water with the possibility of recycling. Copper-free Sonogashira and Heck reaction were also made possible.

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41

Su, Yijin, and Ning Jiao. "Palladium-Catalyzed Oxidative Heck Reaction." Current Organic Chemistry 15, no. 18 (2011): 3362–88. http://dx.doi.org/10.2174/138527211797248030.

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42

Yang, Xiaomei, Sha Ma, Yanni Du, and Yunhai Tao. "Progress in Reductive Heck Reaction." Chinese Journal of Organic Chemistry 33, no. 11 (2013): 2325. http://dx.doi.org/10.6023/cjoc201303053.

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43

Bhattacharya, S., S. Majee, R. Mukherjee, and S. Sengupta. "Heck Reaction of 1-Aryltriazenes." Synthetic Communications 25, no. 5 (1995): 651–57. http://dx.doi.org/10.1080/00397919508011402.

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44

Tietze, Lutz, Katja Heitmann, and Thomas Raschke. "Allylsilane Terminated Domino Heck Reaction." Synlett 1, no. 01 (2004): 35–37. http://dx.doi.org/10.1055/s-1997-682.

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45

Gómez-Escalonilla, María José, and Fernando Langa. "Heck reaction on fullerene derivatives." Tetrahedron Letters 49, no. 22 (2008): 3656–58. http://dx.doi.org/10.1016/j.tetlet.2008.03.150.

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46

Shibasaki, M., T. Ohshima, and W. Itano. "ChemInform Abstract: Mizoroki-Heck Reaction." ChemInform 42, no. 42 (2011): no. http://dx.doi.org/10.1002/chin.201142250.

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47

Zayas, Hazit A., David Valade, Zhongfan Jia, and Michael J. Monteiro. "Heck Reactions in Aqueous Miniemulsions." Australian Journal of Chemistry 65, no. 8 (2012): 1090. http://dx.doi.org/10.1071/ch12164.

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Carrying out organic reactions in water-based nanoreactors represents a ‘green’ method for the preparation of organic compounds. This process eliminates the need for solvents, thus reducing the effect of high volumes of solvent on the environment. In this work, we demonstrate a successful Heck cross-coupling reaction, one of the most used approaches to form C–C bonds using a palladium catalyst, in a miniemulsion. The miniemulsion droplet sizes were small (25 to 42 nm), and the reactions resulted in high conversions of three different products with high trans stereoisomers.

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Shaikh, Tanveer Mahamadali, and Fung-E. Hong. "Palladium(II)-catalyzed Heck reaction of aryl halides and arylboronic acids with olefins under mild conditions." Beilstein Journal of Organic Chemistry 9 (August 5, 2013): 1578–88. http://dx.doi.org/10.3762/bjoc.9.180.

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A series of general and selective Pd(II)-catalyzed Heck reactions were investigated under mild reaction conditions. The first protocol has been developed employing an imidazole-based secondary phosphine oxide (SPO) ligated palladium complex (6) as a precatalyst. The catalytic coupling of aryl halides and olefins led to the formation of the corresponding coupled products in excellent yields. A variety of substrates, both electron-rich and electron-poor olefins, were converted smoothly to the targeted products in high yields. Compared with the existing approaches employing SPO–Pd complexes in a

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Zhou, Xiao-Yu, Xia Chen, and Liang-Guang Wang. "Recycled Pd/C-Catalyzed Heck Reaction of 2-Iodoanilines under Ligand-Free Conditions." Synthesis 49, no. 24 (2017): 5364–70. http://dx.doi.org/10.1055/s-0036-1590895.

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Recyclable Pd/C-catalyzed Heck reaction of 2-iodoanilines with acrylate has been developed. The reaction occurred readily in 1,4-dioxane using Pd/C (10 wt%) as catalyst under ligand-free conditions, and the cross-coupling products were obtained with medium to high yield. Gram-scale reactions and recycling of the catalyst were also demonstrated.

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Franzén, Robert. "The Suzuki, the Heck, and the Stille reaction - three versatile methods for the introduction of new C-C bonds on solid support." Canadian Journal of Chemistry 78, no. 7 (2000): 957–62. http://dx.doi.org/10.1139/v00-089.

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Metal-catalyzed coupling reactions are very efficient and reliable methods for the introduction of new carbon-carbon bonds onto molecules attached to a solid support. This review summarizes recent advances in utilizing the three most used methods, the Suzuki reaction, the Heck reaction, and the Stille reaction, in the field of solid phase organic synthesis resulting in small organic molecule libraries.Key words: metal-catalyzed coupling reactions, carbon-carbon bonds, solid phase synthesis, combinatorial chemistry, drug discovery.

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