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Zeitschriftenartikel zum Thema „Reductive reactions“

Autor: Grafiati

Veröffentlicht am 18. Mai 2024

Zuletzt aktualisiert am 31. Juli 2025

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1

Koóš, Peter, Martin Markovič, Pavol Lopatka, and Tibor Gracza. "Recent Applications of Continuous Flow in Homogeneous Palladium Catalysis." Synthesis 52, no. 23 (2020): 3511–29. http://dx.doi.org/10.1055/s-0040-1707212.

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Considerable advances have been made using continuous flow chemistry as an enabling tool in organic synthesis. Consequently, the number of articles reporting continuous flow methods has increased significantly in recent years. This review covers the progress achieved in homogeneous palladium catalysis using continuous flow conditions over the last five years, including C–C/C–N cross-coupling reactions, carbonylations and reductive/oxidative transformations.1 Introduction2 C–C Cross-Coupling Reactions3 C–N Coupling Reactions4 Carbonylation Reactions5 Miscellaneous Reactions6 Key to Schematic Sy

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2

Nicholas, Kenneth M., and Chandrasekhar Bandari. "Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides." Synthesis 53, no. 02 (2020): 267–78. http://dx.doi.org/10.1055/s-0040-1707269.

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AbstractThe prospective utilization of abundant, CO2-neutral, renewable feedstocks is driving the discovery and development of new reactions that refunctionalize oxygen-rich substrates such as alcohols and polyols through C–O bond activation. In this review, we highlight the development of transition-metal-promoted reactions of renewable alcohols and epoxides that result in carbon–carbon bond-formation. These include reductive self-coupling reactions and cross-coupling reactions of alcohols with alkenes and arene derivatives. Early approaches to reductive couplings employed stoichiometric amou

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3

R., G. BHATTACHARYYA. "Systematisation of Synthetic Inorganic Reactions. Part-l. Electron-transfer Reactions : Possibility of introducing Name Reactions in Inorganic Chemistry." Journal Of India Chemical Society Vol.66, Aug-Oct 1989 (1989): 579–83. https://doi.org/10.5281/zenodo.5996445.

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Department of Chemistry, Jadavpur University, Calcutta- 700 032 Synthetic reactions in inorganic and coordination chemistry have not grown systematically. Since inorganic chemistry encompasses a variety of elements it is difficult to systematise those synthetic reactions. An attention has herein been focussed on the reductive reaction of higher valent metal ions with a view to generalising some synthetic routes. The concerned area is reductive nitrosylation and reductive carbonylation. It has been suggested that perhaps the introduction of name reactions, par

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4

Dutta, Lona, Atanu Mondal, and S. S. V. Ramasastry. "Metal‐Free Reductive Aldol Reactions." Asian Journal of Organic Chemistry 10, no. 4 (2021): 680–91. http://dx.doi.org/10.1002/ajoc.202000693.

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5

Pal, Sudipta, You-Yun Zhou, and Christopher Uyeda. "Catalytic Reductive Vinylidene Transfer Reactions." Journal of the American Chemical Society 139, no. 34 (2017): 11686–89. http://dx.doi.org/10.1021/jacs.7b05901.

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6

Lin, Ivan J. B., Hayder A. Zahalka, and Howard Alper. "Rhodium catalyzed reductive esterification reactions." Tetrahedron Letters 29, no. 15 (1988): 1759–62. http://dx.doi.org/10.1016/s0040-4039(00)82035-3.

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7

Anderson, James C., Alexander J. Blake, Paul J. Koovits, and Gregory J. Stepney. "Diastereoselective Reductive Nitro-Mannich Reactions." Journal of Organic Chemistry 77, no. 10 (2012): 4711–24. http://dx.doi.org/10.1021/jo300535h.

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8

Werth, Jacob, Kristen Berger, and Christopher Uyeda. "Cobalt Catalyzed Reductive Spirocyclopropanation Reactions." Advanced Synthesis & Catalysis 362, no. 2 (2019): 348–52. http://dx.doi.org/10.1002/adsc.201901293.

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9

Wang, Zhipeng A., Yan-Yu Liang, and Ji-Shen Zheng. "Reductive Amination/Alkylation Reactions: The Recent Developments, Progresses, and Applications in Protein Chemical Biology Studies." Current Organic Synthesis 15, no. 6 (2018): 755–61. http://dx.doi.org/10.2174/1570179415666180522093905.

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The chemical modifications of proteins or protein complexes have been a challenging but fruitful task in the post-genomic era. Bioorthogonal reactions play an important role for the purpose of selective functionalization, localization, and labeling of proteins with natural or non-natural structures. Among these reactions, reductive amination stands out as one of the typical bioorthogonal reactions with high efficiency, good biocompatibility, and versatile applications. However, not many specific reviews exist to discuss the mechanism, kinetics, and their applications in a detailed manner. In t

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10

Beeler, Joshua A., and Henry S. White. "Reductive Electrosynthesis Initiated By Mediated Oxalate Oxidation." ECS Meeting Abstracts MA2024-02, no. 53 (2024): 3639. https://doi.org/10.1149/ma2024-02533639mtgabs.

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Reductive electrosynthesis often requires large negative potentials, air-sensitive electrocatalysts, precious metal electrode surfaces, dry solvent, and/or a sacrificial anode. As a result, electroorganic reduction reactions remain relatively underdeveloped compared to oxidative electroorganic methods. This work introduces a novel reductive electrosynthetic method, wherein the mediated oxidation of oxalate (C2O4 2–) at a carbon electrode facilitates the homogeneous reduction of aryl halides. Specifically, the homogeneous oxidation of C2O4 2– in mixed organic/aqueous solutions by electrochemica

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11

Wang, Yuling, and Qinghua Ren. "DFT Study of the Mechanisms of Transition-Metal-Catalyzed Reductive Coupling Reactions." Current Organic Chemistry 24, no. 12 (2020): 1367–83. http://dx.doi.org/10.2174/1385272824999200608135840.

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The mechanism studies of transition-metal-catalyzed reductive coupling reactions investigated using Density Functional Theory calculations in the recent ten years have been reviewed. This review introduces the computational mechanism studies of Ni-, Pd-, Cu- and some other metals (Rh, Ti and Zr)-catalyzed reductive coupling reactions and presents the methodology used in these computational mechanism studies. The mechanisms of the transition- metal-catalyzed reductive coupling reactions normally include three main steps: oxidative addition; transmetalation; and reductive elimination or four mai

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12

Zhou, You-Yun, and Christopher Uyeda. "Catalytic reductive [4 + 1]-cycloadditions of vinylidenes and dienes." Science 363, no. 6429 (2019): 857–62. http://dx.doi.org/10.1126/science.aau0364.

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Cycloaddition reactions provide direct and convergent routes to cycloalkanes, making them valuable targets for the development of synthetic methods. Whereas six-membered rings are readily accessible from Diels-Alder reactions, cycloadditions that generate five-membered rings are comparatively limited in scope. Here, we report that dinickel complexes catalyze [4 + 1]-cycloaddition reactions of 1,3-dienes. The C1partner is a vinylidene equivalent generated from the reductive activation of a 1,1-dichloroalkene in the presence of stoichiometric zinc. Intermolecular and intramolecular variants of t

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13

Wu, Hongli, Shuo-Qing Zhang, and Xin Hong. "Mechanisms of nickel-catalyzed reductive cross-coupling reactions." Chemical Synthesis 3, no. 4 (2023): 39. http://dx.doi.org/10.20517/cs.2023.20.

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Nickel-catalyzed reductive cross-coupling (RCC) reactions using two carbon electrophiles as coupling partners provide one of the most reliable and straightforward protocols for facile construction of valuable C-C bonds in the realm of organic chemistry. In recent years, significant progress has been made in the methodological developments and mechanistic studies of these reactions. This review summarizes four widely accepted mechanisms for RCC reactions that have been proposed by experiments or density functional theory calculations. The major difference between these four types of mechanisms

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14

Paterson, Lorna A., Sandra E. Hill, John R. Mitchell, and John M. V. Blanshard. "Sulphite and oxidative—reductive depolymerization reactions." Food Chemistry 60, no. 2 (1997): 143–47. http://dx.doi.org/10.1016/s0308-8146(95)00253-7.

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15

Donohoe, Timothy J., Karl W. Ace, Paul M. Guyo, Madeleine Helliwell, and Jeffrey McKenna. "Reductive aldol reactions on aromatic heterocycles." Tetrahedron Letters 41, no. 7 (2000): 989–93. http://dx.doi.org/10.1016/s0040-4039(99)02224-8.

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16

Hawkins, Bill C., Paul A. Keller, and Stephen G. Pyne. "Reductive ring opening reactions of diphenyldihydrofullerenylpyrroles." Tetrahedron Letters 48, no. 42 (2007): 7533–36. http://dx.doi.org/10.1016/j.tetlet.2007.08.044.

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17

Panfilov, A. V., Yu D. Markovich, I. P. Ivashev, et al. "Sodium borohydride in reductive amination reactions." Pharmaceutical Chemistry Journal 34, no. 2 (2000): 76–78. http://dx.doi.org/10.1007/bf02524364.

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18

Bochkarev, M. N., and L. V. Pankratov. "Principles of oxidative-reductive transmetallation reactions." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 36, no. 8 (1987): 1717–22. http://dx.doi.org/10.1007/bf00960141.

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19

Cadoux, Cécile, and Ross D. Milton. "Recent Enzymatic Electrochemistry for Reductive Reactions." ChemElectroChem 7, no. 9 (2020): 1974–86. http://dx.doi.org/10.1002/celc.202000282.

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20

Valdés, Carlos, Miguel Paraja, and Manuel Plaza. "Transition-Metal-Free Reactions Between Boronic Acids and N-Sulfonylhydrazones or Diazo Compounds: Reductive Coupling Processes and Beyond." Synlett 28, no. 18 (2017): 2373–89. http://dx.doi.org/10.1055/s-0036-1590868.

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The metal-free reaction between diazo compounds and boronic acids has been established in recent years as a powerful C(sp3)–C bond-forming reaction. This account covers the recent advances in this area. First, the various synthetic applications of reactions with N-sulfonylhydrazones as a convenient source of diazo compounds is discussed. These transformations can be regarded as reductive couplings of carbonyl compounds. Also covered is the incorporation of other mild sources of diazo compounds in these reactions: diazotization of amines and oxidation of hydrazones. Finally, the development of

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21

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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22

Mitsudome, Takato. "Air-Stable and Highly Active Transition Metal Phosphide Catalysts for Reductive Molecular Transformations." Catalysts 14, no. 3 (2024): 193. http://dx.doi.org/10.3390/catal14030193.

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This review introduces transition metal phosphide nanoparticle catalysts as highly efficient and reusable heterogeneous catalysts for various reductive molecular transformations. These transformations include the hydrogenation of nitriles to primary amines, reductive amination of carbonyl compounds, and biomass conversion, specifically, the aqueous hydrogenation reaction of mono- and disaccharides to sugar alcohols. Unlike traditional air-unstable non-precious metal catalysts, these are stable in air, eliminating the need for strict anaerobic conditions or pre-reduction. Moreover, when combine

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23

Sarhan, Abd El-Wareth A. O. "[4 + 3]Cycloaddition Reactions: Synthesis of 9,10-Dimethoxy-9,10-propanoanthracen-12-ones." Journal of Chemical Research 23, no. 1 (1999): 24–25. http://dx.doi.org/10.1177/174751989902300118.

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Cycloaddition of 9,10-dimethoxyanthracene (1) to tetrabromoacetone (2a) under a variety of conditions afforded isomers 3a,b; reductive debromination of 3a,b afforded 4, while reduction with NaBH4 gave alcohol 6 which on reductive debromination gave olefin 7; reaction of 1 with 2b gave isomers 8a,b.

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24

Rietveld, Patrick, L. David Arscott, Alan Berry, et al. "Reductive and Oxidative Half-Reactions of Glutathione Reductase from Escherichia coli." Biochemistry 33, no. 46 (1994): 13888–95. http://dx.doi.org/10.1021/bi00250a043.

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25

Nokami, Toshiki, Titli Ghosh, Hazuki Kaizawa, Norihiko Sasaki, Manabu Abe, and Takashi Nishikata. "Development of Electrochemical Reductive C-O/C-N Bond Forming Reactions." ECS Meeting Abstracts MA2024-02, no. 53 (2024): 3636. https://doi.org/10.1149/ma2024-02533636mtgabs.

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Development of sterically congested C-O/C-N bond forming reactions are highly desired because these bonds are difficult to construct using conventional methods. Initially we have found that cesium carbonate mediates coupling reactions between α-bromocarboxyamide and alcohols and this method is useful to synthesize sterically congested C-O bonds.1 Based on our proposal of the reaction mechanism we envisioned that this reaction might proceed under electrochemical conditions. Here we report an electrochemical approach to form C-O/C-N bonds of alkyl halides and alcohols/amines under electrochemica

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26

Mikesell, Peter, Michael Schwaebe, Marcello DiMare, et al. "Electrochemical Reductive Coupling Reactions of Aliphatic Nitroalkenes." Acta Chemica Scandinavica 53 (1999): 792–99. http://dx.doi.org/10.3891/acta.chem.scand.53-0792.

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27

Tortajada, Andreu, Marino Börjesson, and Ruben Martin. "Nickel-Catalyzed Reductive Carboxylation and Amidation Reactions." Accounts of Chemical Research 54, no. 20 (2021): 3941–52. http://dx.doi.org/10.1021/acs.accounts.1c00480.

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28

Nozawa-Kumada, Kanako, Shungo Ito, Koto Noguchi, Masanori Shigeno, and Yoshinori Kondo. "Super electron donor-mediated reductive desulfurization reactions." Chemical Communications 55, no. 86 (2019): 12968–71. http://dx.doi.org/10.1039/c9cc06775b.

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29

Poremba, Kelsey E., Sara E. Dibrell, and Sarah E. Reisman. "Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions." ACS Catalysis 10, no. 15 (2020): 8237–46. http://dx.doi.org/10.1021/acscatal.0c01842.

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30

Zhao, Gui-Ling, and Armando Córdova. "Direct organocatalytic asymmetric reductive Mannich-type reactions." Tetrahedron Letters 47, no. 42 (2006): 7417–21. http://dx.doi.org/10.1016/j.tetlet.2006.08.063.

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31

Klatte, Stephanie, Elisabeth Lorenz, and Volker F. Wendisch. "Whole cell biotransformation for reductive amination reactions." Bioengineered 5, no. 1 (2013): 56–62. http://dx.doi.org/10.4161/bioe.27151.

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32

Polidoro, Daniele, Daily Rodriguez-Padron, Alvise Perosa, Rafael Luque, and Maurizio Selva. "Chitin-Derived Nanocatalysts for Reductive Amination Reactions." Materials 16, no. 2 (2023): 575. http://dx.doi.org/10.3390/ma16020575.

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Chitin, the second most abundant biopolymer in the planet after cellulose, represents a renewable carbon and nitrogen source. A thrilling opportunity for the valorization of chitin is focused on the preparation of biomass-derived N-doped carbonaceous materials. In this contribution, chitin-derived N-doped carbons were successfully prepared and functionalized with palladium metal nanoparticles. The physicochemical properties of these nanocomposites were investigated following a multi-technique strategy and their catalytic activity in reductive amination reactions was explored. In particular, a

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33

Anderson, James C., Alexander J. Blake, Paul J. Koovits, and Gregory J. Stepney. "ChemInform Abstract: Diastereoselective Reductive Nitro-Mannich Reactions." ChemInform 43, no. 37 (2012): no. http://dx.doi.org/10.1002/chin.201237038.

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34

Knappke, Christiane E. I., Sabine Grupe, Dominik Gärtner, Martin Corpet, Corinne Gosmini, and Axel Jacobi von Wangelin. "Reductive Cross-Coupling Reactions between Two Electrophiles." Chemistry - A European Journal 20, no. 23 (2014): 6828–42. http://dx.doi.org/10.1002/chem.201402302.

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35

Baxter, R. M. "Reductive Dehalogenation of Environmental Contaminants: A Critical Review." Water Quality Research Journal 24, no. 2 (1989): 299–322. http://dx.doi.org/10.2166/wqrj.1989.018.

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Abstract It is generally recognized that reductive processes are more important than oxidative ones in transforming, degrading and mineralizing many environmental contaminants. One process of particular importance is reductive dehalogenation, i.e., the replacement of a halogen atom (most commonly a chlorine atom) by a hydrogen atom. A number of different mechanisms are involved in these reactions. Photochemical reactions probably play a role in some instances. Aliphatic compounds such as chloroethanes, partly aliphatic compounds such as DDT, and alicyclic compounds such as hexachlorocyclohexan

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36

Chitnis, Saurabh S., Alasdair P. M. Robertson, Neil Burford, Jan J. Weigand, and Roland Fischer. "Synthesis and reactivity of cyclo-tetra(stibinophosphonium) tetracations: redox and coordination chemistry of phosphine–antimony complexes." Chemical Science 6, no. 4 (2015): 2559–74. http://dx.doi.org/10.1039/c4sc03939d.

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37

Rayabarapu, Dinesh Kumar, and Chien-Hong Cheng. "Novel cyclization and reductive coupling of bicyclic olefins with alkyl propiolates catalyzed by nickel complexes." Pure and Applied Chemistry 74, no. 1 (2002): 69–75. http://dx.doi.org/10.1351/pac200274010069.

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In this article, new metal-mediated cyclization and reductive coupling reactions of bicyclic olefins with alkynes are described. Oxabicyclic alkenes undergo cyclization with alkyl propiolates at 80 C catalyzed by nickel complexes to give benzocoumarin derivatives in high yields. The reaction of bicyclic alkenes (oxa- and azacyclic alkenes) with alkyl propiolates at room temperature in the presence of the same nickel complex gave 1,2-dihydro-napthelene derivatives in good-to-excellent yields. This reductive coupling reaction proceeds under very mild conditions in complete regio- and stereoselec

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38

Boll, Matthias, and Georg Fuchs. "Unusual reactions involved in anaerobic metabolism of phenolic compounds." Biological Chemistry 386, no. 10 (2005): 989–97. http://dx.doi.org/10.1515/bc.2005.115.

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AbstractAerobic bacteria use molecular oxygen as a common co-substrate for key enzymes of aromatic metabolism. In contrast, in anaerobes all oxygen-dependent reactions are replaced by a set of alternative enzymatic processes. The anaerobic degradation of phenol to a non-aromatic product involves enzymatic processes that are uniquely found in the aromatic metabolism of anaerobic bacteria: (i) ATP-dependent phenol carboxylation to 4-hydroxybenzoate via a phenylphosphate intermediate (biological Kolbe-Schmitt carboxylation); (ii) reductive dehydroxylation of 4-hydroxybenzoyl-CoA to benzoyl-CoA; a

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39

Vorbeck, Claudia, Hiltrud Lenke, Peter Fischer, Jim C. Spain, and Hans-Joachim Knackmuss. "Initial Reductive Reactions in Aerobic Microbial Metabolism of 2,4,6-Trinitrotoluene." Applied and Environmental Microbiology 64, no. 1 (1998): 246–52. http://dx.doi.org/10.1128/aem.64.1.246-252.1998.

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ABSTRACT Because of its high electron deficiency, initial microbial transformations of 2,4,6-trinitrotoluene (TNT) are characterized by reductive rather than oxidation reactions. The reduction of the nitro groups seems to be the dominating mechanism, whereas hydrogenation of the aromatic ring, as described for picric acid, appears to be of minor importance. Thus, two bacterial strains enriched with TNT as a sole source of nitrogen under aerobic conditions, a gram-negative strain called TNT-8 and a gram-positive strain called TNT-32, carried out nitro-group reduction. In contrast, both a picric

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40

Bacon, Mark, and W. John Ingledew. "The reductive reactions ofThiobacillus ferrooxidanson sulphur and selenium." FEMS Microbiology Letters 58, no. 2-3 (1989): 189–94. http://dx.doi.org/10.1111/j.1574-6968.1989.tb03042.x.

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41

Chiu, Pauline, and Wing Chung. "Reductive Intramolecular Henry Reactions Induced by Stryker’s Reagent." Synlett 2005, no. 01 (2004): 55–58. http://dx.doi.org/10.1055/s-2004-836044.

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42

Molander, Gary A., and Caryn Kenny. "Intramolecular reductive coupling reactions promoted by samarium diiodide." Journal of the American Chemical Society 111, no. 21 (1989): 8236–46. http://dx.doi.org/10.1021/ja00203a027.

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43

Studer, Armido, and Stephan Amrein. "Tin Hydride Substitutes in Reductive Radical Chain Reactions." Synthesis 2002, no. 07 (2002): 835–49. http://dx.doi.org/10.1055/s-2002-28507.

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44

Donohoe, Timothy J., Karl W. Ace, Paul M. Guyo, Madeleine Helliwell, and Jeffrey McKenna. "ChemInform Abstract: Reductive Aldol Reactions on Aromatic Heterocycles." ChemInform 31, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.200018084.

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45

Fürstner, Alois. "Synthesis and Reductive Elimination Reactions of Aryl Thioglycosides." Liebigs Annalen der Chemie 1993, no. 11 (1993): 1211–17. http://dx.doi.org/10.1002/jlac.1993199301196.

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46

Streuff, Jan. "Reductive Umpolung Reactions with Low-Valent Titanium Catalysts." Chemical Record 14, no. 6 (2014): 1100–1113. http://dx.doi.org/10.1002/tcr.201402058.

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47

Czaplik, Waldemar M., Matthias Mayer, and Axel Jacobi von Wangelin. "Iron-Catalyzed Reductive Aryl-Alkenyl Cross-Coupling Reactions." ChemCatChem 3, no. 1 (2010): 135–38. http://dx.doi.org/10.1002/cctc.201000276.

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48

Back, Thomas G. "ChemInform Abstract: Free-Radical Reactions and Reductive Deselenations." ChemInform 31, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.200032234.

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49

Reichard, Holly A., Martin McLaughlin, Ming Z. Chen, and Glenn C. Micalizio. "Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes." European Journal of Organic Chemistry 2010, no. 3 (2010): 391–409. http://dx.doi.org/10.1002/ejoc.200901094.

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50

Roy, Sayan, Divya Garg, and Christopher Uyeda. "Catalytic reductive annulation reactions of alkenes using dihaloalkanes." Tetrahedron Letters 168 (September 2025): 155705. https://doi.org/10.1016/j.tetlet.2025.155705.

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