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Search Results (10)

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Keywords = Kumada cross-coupling

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23 pages, 4563 KiB  
Review
Advances in Cross-Coupling Reactions Catalyzed by Aromatic Pincer Complexes Based on Earth-Abundant 3d Metals (Mn, Fe, Co, Ni, Cu)
by Jesús Antonio Cruz-Navarro, Arturo Sánchez-Mora, Juan S. Serrano-García, Andrés Amaya-Flórez, Raúl Colorado-Peralta, Viviana Reyes-Márquez and David Morales-Morales
Catalysts 2024, 14(1), 69; https://doi.org/10.3390/catal14010069 - 16 Jan 2024
Cited by 5 | Viewed by 5091
Abstract
The increase of noble-metal-free catalysis in organic chemistry is a trending topic in constant growth due to the price increase of noble metals and their scarce abundance. As a result, many earth-abundant transition-metal complexes containing nickel, iron, or cobalt have been successfully applied [...] Read more.
The increase of noble-metal-free catalysis in organic chemistry is a trending topic in constant growth due to the price increase of noble metals and their scarce abundance. As a result, many earth-abundant transition-metal complexes containing nickel, iron, or cobalt have been successfully applied in the homogeneous catalysis of a wide number of cross-coupling reactions, and the use of pincer complexes based on these earth-abundant metals was recently explored, affording interesting results. Thus, this review provides a general overview of earth-abundant 3D pincer complexes and their application during the last decade as catalysts in cross-coupling reactions such as Kumada–Corriu, Suzuki–Miyaura, Sonogashira, C–S cross-coupling, and C–N bond-forming reactions. Full article
(This article belongs to the Special Issue Organometallic Homogeneous Catalysis)
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9 pages, 1218 KiB  
Communication
Facile Attachment of Halides and Pseudohalides to Dodecaborate(2-) via Pd-catalyzed Cross-Coupling
by Mahmoud K. Al-Joumhawy, Jui-Chi Chang, Fariba Sabzi and Detlef Gabel
Molecules 2023, 28(7), 3245; https://doi.org/10.3390/molecules28073245 - 5 Apr 2023
Cited by 8 | Viewed by 2454
Abstract
Cross-coupling reactions with [B12H11I]2− as one partner have been used successfully for Kumada and Buchwald Hartwig couplings with Pd catalysis. Here, we found that the iodide could be substituted easily, and unexpectedly, with other halides such as Br [...] Read more.
Cross-coupling reactions with [B12H11I]2− as one partner have been used successfully for Kumada and Buchwald Hartwig couplings with Pd catalysis. Here, we found that the iodide could be substituted easily, and unexpectedly, with other halides such as Br and Cl, and with pseudohalides such as cyanide, azide, and isocyanate. We found that for Cl, Br, N3, and NCO, tetrabutylammonium salts—or sodium salts—were successful halide sources, whereas for cyanide, CuCN was the only halide source that allowed a successful exchange. The azide could be reacted further in a click reaction with triazoles. While no substitution with fluoride occurred, tetrabutylammonium fluoride in the presence of water led to [B12H11OH]2−. Yields were high to very high, and reaction times were short when using a microwave oven as a heating source. Full article
(This article belongs to the Special Issue New Developments in Boron Chemistry: From Oxidoborates to Hydrido(hetero)borane Derivatives – in Celebration of Professor John D. Kennedy’s 80th Birthday)
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18 pages, 7431 KiB  
Article
Sequential Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Chlorobenzamides/Chemoselective Amide Reduction and Reductive Deuteration to Benzylic Alcohols
by Elwira Bisz, Pamela Podchorodecka, Hengzhao Li, Wioletta Ochędzan-Siodłak, Jie An and Michal Szostak
Molecules 2023, 28(1), 223; https://doi.org/10.3390/molecules28010223 - 27 Dec 2022
Cited by 2 | Viewed by 3291
Abstract
Benzylic alcohols are among the most important intermediates in organic synthesis. Recently, the use of abundant metals has attracted significant attention due to the issues with the scarcity of platinum group metals. Herein, we report a sequential method for the synthesis of benzylic [...] Read more.
Benzylic alcohols are among the most important intermediates in organic synthesis. Recently, the use of abundant metals has attracted significant attention due to the issues with the scarcity of platinum group metals. Herein, we report a sequential method for the synthesis of benzylic alcohols by a merger of iron catalyzed cross-coupling and highly chemoselective reduction of benzamides promoted by sodium dispersion in the presence of alcoholic donors. The method has been further extended to the synthesis of deuterated benzylic alcohols. The iron-catalyzed Kumada cross-coupling exploits the high stability of benzamide bonds, enabling challenging C(sp2)–C(sp3) cross-coupling with alkyl Grignard reagents that are prone to dimerization and β-hydride elimination. The subsequent sodium dispersion promoted reduction of carboxamides proceeds with full chemoselectivity for the C–N bond cleavage of the carbinolamine intermediate. The method provides access to valuable benzylic alcohols, including deuterium-labelled benzylic alcohols, which are widely used as synthetic intermediates and pharmacokinetic probes in organic synthesis and medicinal chemistry. The combination of two benign metals by complementary reaction mechanisms enables to exploit underexplored avenues for organic synthesis. Full article
(This article belongs to the Special Issue Metal-Induced Molecule Activation and Coupling Reactions)
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24 pages, 7362 KiB  
Communication
Nickel-Catalyzed Kumada Cross-Coupling Reactions of Benzylic Sulfonamides
by Kirsten A. Hewitt, Claire A. Herbert, Alissa C. Matus and Elizabeth R. Jarvo
Molecules 2021, 26(19), 5947; https://doi.org/10.3390/molecules26195947 - 30 Sep 2021
Cited by 1 | Viewed by 4652
Abstract
Herein, we report a Kumada cross-coupling reaction of benzylic sulfonamides. The scope of the transformation includes acyclic and cyclic sulfonamide precursors that cleanly produce highly substituted acyclic fragments. Preliminary data are consistent with a stereospecific mechanism that allows for a diastereoselective reaction. Full article
(This article belongs to the Special Issue A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian)
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15 pages, 12940 KiB  
Article
Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates
by Elwira Bisz
Molecules 2021, 26(19), 5895; https://doi.org/10.3390/molecules26195895 - 29 Sep 2021
Cited by 5 | Viewed by 3656
Abstract
Aryl sulfonate esters are versatile synthetic intermediates in organic chemistry as well as attractive architectures due to their bioactive properties. Herein, we report the synthesis of alkyl-substituted benzenesulfonate esters by iron-catalyzed C(sp2)–C(sp3) cross-coupling of Grignard reagents with aryl chlorides. [...] Read more.
Aryl sulfonate esters are versatile synthetic intermediates in organic chemistry as well as attractive architectures due to their bioactive properties. Herein, we report the synthesis of alkyl-substituted benzenesulfonate esters by iron-catalyzed C(sp2)–C(sp3) cross-coupling of Grignard reagents with aryl chlorides. The method operates using an environmentally benign and sustainable iron catalytic system, employing benign urea ligands. A broad range of chlorobenzenesulfonates as well as challenging alkyl organometallics containing β-hydrogens are compatible with these conditions, affording alkylated products in high to excellent yields. The study reveals that aryl sulfonate esters are the most reactive activating groups for iron-catalyzed alkylative C(sp2)–C(sp3) cross-coupling of aryl chlorides with Grignard reagents. Full article
(This article belongs to the Special Issue Ligands in Catalysis)
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40 pages, 17382 KiB  
Review
Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions
by Ioannis D. Kostas and Barry R. Steele
Catalysts 2020, 10(10), 1107; https://doi.org/10.3390/catal10101107 - 24 Sep 2020
Cited by 32 | Viewed by 6950
Abstract
Catalysis of cross-coupling reactions under phosphane-free conditions represents an important ongoing challenge. Although transition metal complexes based on the thiosemicarbazone unit have been known for a very long time, their use in homogeneous catalysis has been studied only relatively recently. In particular, reports [...] Read more.
Catalysis of cross-coupling reactions under phosphane-free conditions represents an important ongoing challenge. Although transition metal complexes based on the thiosemicarbazone unit have been known for a very long time, their use in homogeneous catalysis has been studied only relatively recently. In particular, reports of cross-coupling catalytic reactions with such complexes have appeared only in the last 15 years. This review provides a survey of the research in this area and a discussion of the prospects for future developments. Full article
(This article belongs to the Special Issue Transition Metal Catalyzed Cross-Coupling Reactions)
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13 pages, 3680 KiB  
Article
Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents
by Elwira Bisz and Michal Szostak
Molecules 2020, 25(1), 230; https://doi.org/10.3390/molecules25010230 - 6 Jan 2020
Cited by 14 | Viewed by 6724
Abstract
Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts [...] Read more.
Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)–O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings. Full article
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
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35 pages, 11797 KiB  
Review
Microwave-Assisted Palladium-Catalyzed Cross-Coupling Reactions: Generation of Carbon–Carbon Bond
by Kifah S. M. Salih and Younis Baqi
Catalysts 2020, 10(1), 4; https://doi.org/10.3390/catal10010004 - 18 Dec 2019
Cited by 54 | Viewed by 15536
Abstract
Cross-coupling reactions furnishing carbon–carbon (C–C) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Negishi, Heck, Kumada, Sonogashira, Stille, Suzuki, and Hiyama, utilizing palladium or its salts as catalysis have, for decades, attracted and inspired [...] Read more.
Cross-coupling reactions furnishing carbon–carbon (C–C) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Negishi, Heck, Kumada, Sonogashira, Stille, Suzuki, and Hiyama, utilizing palladium or its salts as catalysis have, for decades, attracted and inspired researchers affiliated with academia and industry. Tremendous efforts have been paid to develop and achieve more sustainable reaction conditions, such as the reduction in energy consumption by applying the microwave irradiation technique. Chemical reactions under controlled microwave conditions dramatically reduce the reaction time and therefore resulting in increase in the yield of the desired product by minimizing the formation of side products. In this review, we mainly focus on the recent advances and applications of palladium catalyzed cross-coupling carbon–carbon bond formation under microwave technology. Full article
(This article belongs to the Section Catalysis in Organic and Polymer Chemistry)
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13 pages, 5353 KiB  
Article
Mechanistic Implications for the Ni(I)-Catalyzed Kumada Cross-Coupling Reaction
by Linda Iffland, Anette Petuker, Maurice Van Gastel and Ulf-Peter Apfel
Inorganics 2017, 5(4), 78; https://doi.org/10.3390/inorganics5040078 - 14 Nov 2017
Cited by 28 | Viewed by 7540
Abstract
Herein we report on the cross-coupling reaction of phenylmagnesium bromide with aryl halides using the well-defined tetrahedral Ni(I) complex, [(Triphos)NiICl] (Triphos = 1,1,1-tris(diphenylphosphinomethyl)ethane). In the presence of 0.5 mol % [(Triphos)NiICl], good to excellent yields (75–97%) of the respective [...] Read more.
Herein we report on the cross-coupling reaction of phenylmagnesium bromide with aryl halides using the well-defined tetrahedral Ni(I) complex, [(Triphos)NiICl] (Triphos = 1,1,1-tris(diphenylphosphinomethyl)ethane). In the presence of 0.5 mol % [(Triphos)NiICl], good to excellent yields (75–97%) of the respective coupling products within a reaction time of only 2.5 h at room temperature were achieved. Likewise, the tripodal Ni(II)complexes [(κ2-Triphos)NiIICl2] and [(κ3-Triphos)NiIICl](X) (X = ClO4, BF4) were tested as potential pre-catalysts for the Kumada cross-coupling reaction. While the Ni(II) complexes also afford the coupling products in comparable yields, mechanistic investigations by UV/Vis and electron paramagnetic resonance (EPR) spectroscopy indicate a Ni(I) intermediate as the catalytically active species in the Kumada cross-coupling reaction. Based on experimental findings and density functional theory (DFT) calculations, a plausible Ni(I)-catalyzed reaction mechanism for the Kumada cross-coupling reaction is presented. Full article
(This article belongs to the Special Issue Revealing Reaction Mechanisms in Homogeneous Transition Metal Catalysis)
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29 pages, 1234 KiB  
Review
Advances in Metal-Catalyzed Cross-Coupling Reactions of Halogenated Quinazolinones and Their Quinazoline Derivatives
by Malose Jack Mphahlele and Marole Maria Maluleka
Molecules 2014, 19(11), 17435-17463; https://doi.org/10.3390/molecules191117435 - 29 Oct 2014
Cited by 31 | Viewed by 10674
Abstract
Halogenated quinazolinones and quinazolines are versatile synthetic intermediates for the metal-catalyzed carbon–carbon bond formation reactions such as the Kumada, Stille, Negishi, Sonogashira, Suzuki-Miyaura and Heck cross-coupling reactions or carbon-heteroatom bond formation via the Buchwald-Hartwig cross-coupling to yield novel polysubstituted derivatives. This review presents [...] Read more.
Halogenated quinazolinones and quinazolines are versatile synthetic intermediates for the metal-catalyzed carbon–carbon bond formation reactions such as the Kumada, Stille, Negishi, Sonogashira, Suzuki-Miyaura and Heck cross-coupling reactions or carbon-heteroatom bond formation via the Buchwald-Hartwig cross-coupling to yield novel polysubstituted derivatives. This review presents an overview of the application of these methods on halogenated quinazolin-4-ones and their quinazolines to generate novel polysubstituted derivatives. Full article
(This article belongs to the Section Organic Chemistry)
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