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Journal articles on the topic "Cross Reactions"

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Pires, Marina, Sara Purificação, A. Santos, and M. Marques. "The Role of PEG on Pd- and Cu-Catalyzed Cross-Coupling Reactions." Synthesis 49, no. 11 (April 26, 2017): 2337–50. http://dx.doi.org/10.1055/s-0036-1589498.

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Carbon–carbon and carbon–heteroatom coupling reactions are among the most important transformations in organic synthesis as they enable complex structures to be formed from readily available compounds under different routes and conditions. Several metal-catalyzed cross-coupling reactions have been developed creating many efficient methods accessible for the direct formation of new bonds between differently hybridized carbon atoms.During the last decade, much effort has been devoted towards improvement of the sustainability of these reactions, such as catalyst recovery and atom efficiency. Polyethylene glycol (PEG) can be used as a medium, as solid-liquid phase transfer catalyst, or even as a polymer support. PEG has been investigated in a wide variety of cross-coupling reactions either as an alternative solvent to the common organic solvents or as a support for catalyst, substrate, and ligand. In this review we will summarize the different roles of PEG in palladium- and copper-catalyzed cross-coupling reactions, with the focus on Heck, Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig, Stille, Fukuyama, and homocoupling reactions. We will highlight the role of PEG, the preparation of PEGylated catalysts and substrates, and the importance for the reaction outcome and applicability.1 Introduction2 PEG in Heck Reactions3 PEG in Homocoupling Reactions4 PEG in Suzuki–Miyaura Reactions5 PEG in Sonogashira Reactions6 PEG in Buchwald–Hartwig Reactions7 PEG in Stille Reactions8 PEG in Fukuyama Reactions9 PEG in Miscellaneous Cross-Coupling Routes10 Conclusions
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Daley, Ryan A., and Joseph J. Topczewski. "Aryl-Decarboxylation Reactions Catalyzed by Palladium: Scope and Mechanism." Synthesis 52, no. 03 (December 13, 2019): 365–77. http://dx.doi.org/10.1055/s-0039-1690769.

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Palladium-catalyzed cross-couplings and related reactions have enabled many transformations essential to the synthesis of pharmaceuticals, agrochemicals, and organic materials. A related family of reactions that have received less attention are decarboxylative functionalization reactions. These reactions replace the preformed organometallic precursor (e.g., boronic acid or organostannane) with inexpensive and readily available carboxylic acids for many palladium-catalyzed reactions. This review focuses on catalyzed reactions where the elementary decarboxylation step is thought to occur at a palladium center. This review does not include decarboxylative reactions where decarboxylation is thought to be facilitated by a second metal (copper or silver) and is specifically limited to (hetero)arenecarboxylic acids. This review includes a discussion of oxidative Heck reactions, protodecarboxylation reactions, and cross-coupling reactions among others.1 Introduction2 Oxidative Heck Reactions3 Protodecarboxylation Reactions4 Cross-Coupling Reactions5 Other Reactions6 Conclusion
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Koóš, Peter, Martin Markovič, Pavol Lopatka, and Tibor Gracza. "Recent Applications of Continuous Flow in Homogeneous Palladium Catalysis." Synthesis 52, no. 23 (August 3, 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 Symbols7 Conclusion
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Staubitz, Anne, Melanie Walther, Waldemar Kipke, Sven Schultzke, and Souvik Ghosh. "Modification of Azobenzenes by Cross-Coupling Reactions." Synthesis 53, no. 07 (January 28, 2021): 1213–28. http://dx.doi.org/10.1055/s-0040-1705999.

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AbstractAzobenzenes are among the most extensively used molecular switches for many different applications. The need to tailor them to the required task often requires further functionalization. Cross-coupling reactions are ideally suited for late-stage modifications. This review provides an overview of recent developments in the modification of azobenzene and its derivatives by cross-coupling reactions.1 Introduction2 Azobenzenes as Formally Electrophilic Components2.1 Palladium Catalysis2.2 Nickel Catalysis2.3 Copper Catalysis2.4 Cobalt Catalysis3 Azobenzenes as Formally Nucleophilic Components3.1 Palladium Catalysis3.2 Copper Catalysis3.3 C–H Activation Reactions4 Azobenzenes as Ligands in Catalysts5 Diazocines5.1 Synthesis5.2 Cross-Coupling Reactions6 Conclusion
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Akkarasamiyo, Sunisa, Somsak Ruchirawat, Poonsaksi Ploypradith, and Joseph S. M. Samec. "Transition-Metal-Catalyzed Suzuki–Miyaura-Type Cross-Coupling Reactions of π-Activated Alcohols." Synthesis 52, no. 05 (January 7, 2020): 645–59. http://dx.doi.org/10.1055/s-0039-1690740.

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The Suzuki–Miyaura reaction is one of the most powerful tools for the formation of carbon–carbon bonds in organic synthesis. The utilization of alcohols in this powerful reaction is a challenging task. This short review covers progress in the transition-metal-catalyzed Suzuki­–Miyaura-type cross-coupling reaction of π-activated alcohol, such as aryl, benzylic, allylic, propargylic and allenic alcohols, between 2000 and June 2019.1 Introduction2 Suzuki–Miyaura Cross-Coupling Reactions of Aryl Alcohols2.1 One-Pot Reactions with Pre-activation of the C–O Bond2.1.1 Palladium Catalysis2.1.2 Nickel Catalysis2.2 Direct Activation of the C–O Bond2.2.1 Nickel Catalysis3 Suzuki–Miyaura-Type Cross-Coupling Reactions of Benzylic Alcohols4 Suzuki–Miyaura-Type Cross-Coupling Reactions of Allylic Alcohols4.1 Rhodium Catalysis4.2 Palladium Catalysis4.3 Nickel Catalysis4.4 Stereospecific Reactions4.5 Stereoselective Reactions4.6 Domino Reactions5 Suzuki–Miyaura-Type Cross-Coupling Reactions of Propargylic Alcohols5.1 Palladium Catalysis5.2 Rhodium Catalysis6 Suzuki–Miyaura-Type Cross-Coupling Reactions of Allenic Alcohols6.1 Palladium Catalysis6.2 Rhodium Catalysis7 Conclusions
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Bolm, Carsten. "Cross-Coupling Reactions." Journal of Organic Chemistry 77, no. 12 (June 15, 2012): 5221–23. http://dx.doi.org/10.1021/jo301069c.

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Bolm, Carsten. "Cross-Coupling Reactions." Organic Letters 14, no. 12 (June 15, 2012): 2925–28. http://dx.doi.org/10.1021/ol301436v.

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Li, Jie, and Paul Knochel. "Chromium-Catalyzed Cross-Couplings and Related Reactions." Synthesis 51, no. 10 (March 21, 2019): 2100–2106. http://dx.doi.org/10.1055/s-0037-1611756.

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Transition-metal-catalyzed cross-couplings have been recognized as a powerful tool for sustainable syntheses. Despite the fact that remarkable progress was achieved by palladium and nickel catalysis, the high price and toxicity still remained a drawback. Recently, naturally more abundant and less toxic low-valent chromium salts, such as Cr(II) and Cr(III) chlorides, displayed notable unique catalytic reactivity. Thus, recent progress in the field of chromium-catalyzed cross-couplings and related reactions are highlighted in the present short review until December­ 2018.1 Introduction and Early Chromium-Mediated Reactions2 Chromium-Catalyzed Cross-Couplings and Related Reactions3 Conclusion
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Verner, Jiří, and Milan Potáček. "Aromatic glyoxalimines in criss-cross cycloaddition reactions." Open Chemistry 2, no. 1 (March 1, 2004): 220–33. http://dx.doi.org/10.2478/bf02476192.

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AbstractAromatic 1,4-diazabuta-1,3-dienes in glacial acetic acid with thiocyanates produce via criss-cross cycloaddition reactions the corresponding perhydroimidazo[4,5-d]imidazole-2,5-dithiones. When a mixture of thiocyanate and cyanate in a proper ratio was reacted together, nonsymmetrical 5-thioxo-perhydroimidazo[4,5-d]imidazole-2-ones were isolated. With cyanates substituted aromatic 1,4-diazabuta-1,3-dienes afforded product of acetic acid addition to primary formed 1,3-dipole intermediate 5-(4-substituted phenylamino)-3-(4-substituted phenyl)-2-oxoimidazolidin-4-yl acetate.
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Galeta, Juraj, Stanislav Man, Aneta Valoušková, and Milan Potáček. "Homoallenyl azines in criss-cross cycloaddition reactions." Monatshefte für Chemie - Chemical Monthly 144, no. 2 (November 7, 2012): 205–16. http://dx.doi.org/10.1007/s00706-012-0865-7.

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Dissertations / Theses on the topic "Cross Reactions"

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Arismendi, Romero Graciela. "Paladium catalized cross-coupling reactions." Revista de Química, 2012. http://repositorio.pucp.edu.pe/index/handle/123456789/101014.

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El premio Nobel en Química de este año ha sido otorgado a los investigadores Richard Heck (EE.UU.), Ei-ichi Negishi (EE.UU.) y Akira Suzuki (Japón), por sus valiosos aportesen el desarrollo de un tipo específico de reacciones para la formación de enlaces C-C: “Reacciones de acoplamientocruzado catalizadas por paladio”. La creciente demanda de nuevas sustancias para el desarrollo de medicamentos, materiales y/o compuestos biológicamente activos ha hecho de este descubrimiento una importante herramienta para los químicos, dándoles la capacidad de atender estas necesidades con la creación de moléculas complejas de utilidad industrial.
This year´s Nobel Prize in Chemistry has been awarded to the researchers Richard Heck (USA), Ei-Ichi Negishi(USA) and Akira Suzuki (Japan), for their valuable contributions to the development of a specific type of reaction for the formation of carbon-carbon bonds: “Palladium-catalyzed cross couplings”. The growing demand for new substances for drug development, materials and/or biologically active compounds has made this discovery an important tool for chemists, giving them the ability to meet these needs through the creation of complex molecules of industrial utility.
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Black, Daniel. "Imines in copper-catalyzed cross-coupling reactions." Thesis, McGill University, 2006. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=102960.

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The purpose of this study was to develop new catalytic methods to mediate carbon-carbon bond forming reactions with imines under mild conditions and in a general manner. We found that copper catalysts were compatible in cross-coupling of a range of mild organometallic reagents, providing simple, efficient routes to alpha-substituted amides and amines.
Chapter 2 of this thesis describes a new copper-catalyzed multicomponent synthesis of alpha-substituted amides. This reaction was developed based upon previous work in this laboratory, which showed that palladium catalysts were competent in Stille-type cross-coupling of imines, acid chlorides, and organostannanes. While providing a mild method of generating the amide products, a more general procedure able to incorporate a wider range of organostannanes was sought. This chapter details the development of a copper-catalyzed protocol, which, as well as performing the cross-coupling under mild reaction conditions, proceeds with a diverse range of aryl-, heteroaryl-, and vinyl-substituted organostannanes and employs an inexpensive and readily available catalyst. Through this system, control over regioselectivity of addition to alpha,beta-unsaturated imines is also possible.
Chapter 3 demonstrates that, in addition to organostannanes, other substrates are viable in copper-catalyzed cross-coupling with imines and acid chlorides. Herein, the coupling of terminal alkynes with imines and acid chlorides is described, leading to an efficient synthesis of tertiary propargylamides directly from simple starting materials. This synthesis incorporates a wide variety of substituted imines, acid chlorides/chloroformates, and terminal alkynes, providing a rapid synthesis of these useful building blocks (reaction completion in only 15 minutes). In addition, the process is shown to work with aza-aromatic heterocycles, such as pyridine, where the alkynylation occurs exclusively at the 2-position.
Chapter 4 describes the utility of these rapid multicomponent reactions, where the products are directly converted into oxazole heterocycles. Copper-catalyzed- and zinc-catalyzed protocols are developed for the synthesis of secondary propargylamides from silyl-imines, acid chlorides, and terminal alkynes. The secondary propargylamide products are then, in a one pot sequence, transformed into trisubstituted oxazoles.
Chapter 5 describes the development of an atom-economical, non-toxic alternative to the organotin coupling described in Chapter 2. This involves the use of tri- and tetraorgano-indium reagents, which can transfer all of their organic groups in a copper-catalyzed coupling with imines and acid chlorides. This reaction shows good functional group compatibility and further expands the scope of alpha-substituted amides and N-protected amines that can be synthesized through mild copper catalysis.
Chapter 6 explores the enantioselective alkynylation of nitrogen-containing heterocycles. As described in Chapter 3, heterocycles such as pyridine can undergo copper-catalyzed 1,2-addition with terminal alkynes upon activation by chloroformates. As this process generates a stereocenter, it is possible to introduce enantio-control into the reactions by using a chiral copper catalyst. With ligands from the PINAP series, enantioselectivities of up to 84% can be induced in the coupling of nitrogen-containing heterocycles (e.g., quinoline), chloroformates, and terminal alkynes. This provides a mild and simple synthesis of chiral 2-alkynyl-1,2-dihydroquinolines directly from simple starting materials.
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Hall, Mark Andrew. "Iron-catalysed cross-coupling and reduction reactions." Thesis, University of Bristol, 2010. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.551314.

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Iron nanoparticles of size 6-16 nm have been successfully prepared by the reduction of FeCb with 3-pentylmagnesium bromide in the presence of polyethylene glycol. These nanoparticles show excellent activity in the catalytic dehalogenation of a range of alkyl and aryl halides when used at 5 mol% loadings, if an excess of the Grignard is present to ensure the regeneration of the catalyst. Alkyl halides react to give mixtures of alkane, alkene and homocoupled products, with good selectivity of the alkane product being observed. Aryl halides undergo hydrodehalogenation cleanly and do not undergo homocoupling. A general methodology, previously developed within the group for the cross-coupling of benzyl halides with diarylzinc reagents has been applied to other substrates. This includes 2-halopyridines and N-(bromomethyl)phthalimide, with the former exhibiting slower reaction rates so higher temperatures were required. Surprisingly, in the case of N-(bromomethyl)phthalimide, the coupling reaction was found to proceed without the need for a catalyst. This has been demonstrated for a number of diarylzinc reagents, which resulted in the cross-coupled product being formed in good to excellent yields. Furthermore,. this substrate undergoes cross- coupling with a range of boronic acids via transmetallation to diethylzinc.
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Zhou, Jianrong (Jianrong Steve). "Cross-coupling reactions of unactivated alkyl halides." Thesis, Massachusetts Institute of Technology, 2005. http://hdl.handle.net/1721.1/33655.

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Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2005.
Vita.
Includes bibliographical references.
My graduate research at MIT has been focused on the development of palladium- or nickel-catalyzed cross-coupling reactions using unactivated alkyl electrophiles (e.g., halides and sulfonates). Although aryl and alkenyl electrophiles have been commonly used in such processes, the utility of alkyl substrates has been underdeveloped, and merits further exploration. We have developed the first palladium-based catalyst that is effective for Negishi couplings of primary alkyl electrophiles. A single protocol (2%Pd₂(dba)₃/8%P(Cyp)₃/NMI in THF/NMP at 80⁰C) can be applied to a broad spectrum of electrophiles, including chlorides, bromides, iodides, and tosylates. Concerning the scope of the nucleophilic components, an array of alkyl-, alkenyl-, and arylzinc halides can be coupled. The process is tolerant of a variety of functional groups, including esters, amides, imides, nitriles, and heterocycles. Furthermore, geometrically- defined alkenylzinc species, generated from titanium-mediated hydrozincation of internal alkynes, can be directly used in the process. Despite the progress in nickel- and palladium-catalyzed C(sp³)-C(sp³) bond formation, the methods had been limited to primary alkyl electrophiles.
(cont.) No doubt, the ability to use more challenging, secondary ones will further augment the usefulness of these metal- catalyzed processes. To this end, we have determined that Ni(cod)₂/s-Bu-Pybox can catalyze room-temperature Negishi couplings of an array of functionalized alkyl bromides and iodides. To the best of our knowledge, this is the first nickel- or palladium- catalyzed cross-coupling procedure for unactivated, [beta]-hydrogen-containing secondary alkyl halides. In addition, preliminary studies using substrate-based probes suggest that the oxidative addition proceeds through a radical pathway. This may explain the unparalleled reactivity of the nickel catalyst. As an extension of the nickel catalysis, we have established that the combination of Ni(cod)₂ and bathophenanthroline can effect Suzuki reactions of secondary halides and organoboronic acids. These organoboron reagents are particularly widely used in the cross-coupling chemistry, owing to their chemical stability, biological non-toxicity, and commercial availability. Again, mechanistic evidence has been collected to support the involvement of organic radicals during the oxidative addition step.
by Jianrong (Steve) Zhou.
Ph.D.
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Moriwaki, Yuya. "Cross-Coupling Reactions in Flow Microreactor Systems." 京都大学 (Kyoto University), 2015. http://hdl.handle.net/2433/200446.

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Adams, Kirsty. "Metal catalysed cross-coupling reactions of heterocycles." Thesis, University of Huddersfield, 2013. http://eprints.hud.ac.uk/id/eprint/20889/.

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This report describes two methodology studies dedicated towards development of metal catalysed crosscoupling reactions in the synthesis of novel heterocyclic compounds. Firstly, a Heck-Mizoroki arylation reaction is reported for the direct functionalisation of tetrahydropyridines, towards the synthesis of kainoid analogues. Kainoids are a group of non-proteinogenic pyrrolidine dicarboxylic acids, which have attracted considerable interest because of their potent biological activity, including insecticidal, anthelmintic and neuroexcitatory properties. The ideal synthesis of kainoids would allow the ability to introduce various side chains at the C-4 position to access diverse pharmacologically active kainoid analogues. Tandem asymmetric Heck-Mizoroki arylation reaction and [2,3]-sigmatropic rearrangement provides a quick and efficient way to access these molecules. The Heck-Mizoroki arylation of 1-methyl-1,2,5,6-tetrahydropyridine and its hydrochloride salt is reported, with the arylation in the 3- position of the tetrahydropyridine as the major product. The reaction has been applied to a variety of substituted aryliodides, with promising results, demonstrating functional group tolerance of the method, however isolation and purification of the resulting compounds has remained challengeing. Diarylation of tetrahydropyridines has also been achieved. Secondly, a new catalytic method for arylative spirocyclisation is reported, using stoichiometric Grignard reagents and iron(III) catalysts, to induce cyclisation of 2-iodo benzyl ethers of furan in a highly stereoselective manner to produce novel functionalised spirocyclic compounds. Method optimisation and application of a variety of Grignard reagents is reported with aryl cross-coupling achieved in high yields. Alkyl- cross coupling has also been achieved with ethylmagnesium bromide Grignard reagent.
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García, Melchor Maximiliano. "Theoretical Study on Pd-catalyzed Cross-Coupling Reactions." Doctoral thesis, Universitat Autònoma de Barcelona, 2012. http://hdl.handle.net/10803/96827.

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D’ençà el seu descobriment, fa ja prop de tres dècades, les reaccions d’acoblament creuat C-C catalitzades per Pd han esdevingut una de les transformacions més poderoses dins la química organometàl·lica. De fet, tres dels desenvolupadors de les reaccions d’acoblament més emprades (reaccions de Heck, Suzuki i Negishi) van ésser guardonats l'any 2010 amb el premi Nobel de Química. El mecanisme general de les reaccions d'acoblament creuat C-C consisteix en tres etapes: addició oxidant, transmetal·lació, i eliminació reductiva. La millora d’una reacció comporta el coneixement profund del seu mecanisme de reacció, o el que és el mateix, la comprenssió del seu funcionament a nivell molecular. Així doncs, aquesta tesi doctoral s'ha centrat en l’estudi del mecanisme de reacció de diferents reaccions d’acoblament creuat C-C catalitzades per Pd: la reacció de Negishi, la reacció de Sonogashira en la seva variant sense coure, i una versió enantioselectiva de la reacció de Suzuki-Miyaura. Tots aquests estudis s'han dut a terme mitjançant càlculs mecano-quàntics i en estreta col·laboració amb grups experimentals de prestigi mundial. En el cas de la reacció de Negishi, s'ha investigat el procés de transmetal·lació amb ZnMeCl i ZnMe2 amb l'objectiu de proporcionar una visió detallada dels respectius mecanismes de reacció. Concretament, per a la transmetal·lació amb ZnMeCl, els càlculs teòrics han mostrat les elevades probabilitats que existeixen de generar-se nous intermedis que donarien lloc a productes d'homo-acoblament no desitjats. Per altra banda, per a la transmetal·lació amb ZnMe2, els resultats teòrics han demostrat l'existència d'intermedis catiònics a priori inesperats. A més, s'han identificat altres mecanismes de transmetal·lació competitius que fins ara no s'havien proposat mai. En resum, en aquest estudi s'ha obtingut una visió detallada dels mecanismes de reacció involucrats en aquestes reaccions. Per a la reacció de Sonogashira sense coure, s'han investigat els dos mecanismes de reacció proposats en la literatura. Els resultats teòrics han permès descartar un d'aquests mecanismes (carbopal·ladació) i han demostrat que l'altre (desprotonació) és factible. A més, l'anàlisi dels mecanístic ha portat a la proposta d'un nou mecanisme de reacció (iònic). Aquest mecanisme consisteix en la desprotonació de l'alquí i la posterior reacció d'aquesta espècie amb el catalitzador de Pd. L'efecte dels substituents en l'alquí en aquests mecanismes de reacció també s'ha analitzat. En termes generals, aquest estudi mecanistic ha revelat que, de la mateixa manera que en altres reaccions d'acoblament, hi ha varis mecanismes competitius i que el canvi de les condicions de reacció (solvent, lligands, substrat, base) pot afavorir un o altre. Finalment, s'ha investigat el mecanisme de reacció per un acoblament assimètric de Suzuki-Miyaura catalitzat per un complex de Pd bis-hidrazona. Els resultats derivats d'aquest estudi han revelat que el mecanisme de transmetal·lació difereix del camí general proposat a la literatura: en aquest cas dos etapes addicionals són necessàries. Aquesta modificació es pot atribuir a la capacitat del lligand bis-hidrazona de dissociar un dels àtoms de N directament coordinat al catalitzador de Pd (comportament hemilàbil). Pel que fa referència a l'estereoquímica de la reacció, els càlculs realitzats fins ara no han pogut donar una explicació clara de les enantioselectivitats observades experimentalment. En resum, els resultsats teòrics obtinguts en aquesta tesi han demostrat que els càculs teòrics són una eina de gran ajut per a l’elucidació i/o proposta de mecanismes de reacció d'aquest tipus de processos.
Since its discovery, nearly three decades ago, the Pd-catalyzed cross-coupling reactions have become one of the most powerful transformations in organometallic chemistry. In fact, three of the developers of the most widely used cross-coupling reactions were awarded in 2010 with the Nobel Prize in Chemistry. The general reaction mechanism for C-C cross-coupling consists in three main steps: oxidative addition, transmetalation, and reductive elimination. The reaction improvement entails a deep knowledge of their complete mechanism, or what is the same thing, how they work at the molecular level. Thus, this thesis has been focused on studying the reaction mechanism for different Pd-catalyzed cross-coupling reactions: the Negishi reaction, the copper-free Sonogashira reaction, and an enantioselective version of the Suzuki-Miyaura reaction. All these studies have been carried out by means of quantum-mechanics calculations and in close collaboration with top experimental groups worldwide. In the case of the Negishi reaction, the transmetalation process with ZnMeCl and ZnMe2 reagents has been investigated in order to provide a detailed picture of their reaction mechanisms. In particular, for the transmetalation with ZnMeCl, calculations have pointed out the many chances for the generation of new intermediates that would eventually give rise to homocoupling side products. On the other hand, for the transmetalation with ZnMe2, the theoretical results have proved the existence of previously unexpected cationic intermediates. Moreover, additional competitive transmetalation pathways for this reaction, some of which had not been invoked before, have been also identified. Overall, in this study a general picture of the reaction mechanisms involved in these reactions has been obtained. For the copper-free Sonogashira reaction, the two reaction mechanisms proposed in the literature have been evaluated. Theoretical results, have been able to discard one of those mechanisms (carbopalladation), whereas the other one (deprotonation) has been found to be feasible. Furthermore, the mechanistic analysis have conducted to the proposal of a new reaction mechanism (ionic). This mechanism involves the deprotonation of the alkyne and the subsequent reaction of this species with the Pd catalyst. The effect of the alkyne's substituents on these reaction mechanisms has been also analyzed. Overall, the mechanistic study reported in this thesis has revealed that, just like in other cross-coupling reaction, there are several competing reaction pathways and a change on the reaction conditions (e.g. solvent, ligands, substrate, base) might favor one over the other ones. Finally, the theoretical investigation on the reaction mechanism for an asymmetric Suzuki-Miyaura coupling catalyzed by a bis-hydrazone Pd catalyst has been carried out. The results derived from this study have revealed that the transmetalation mechanism differs from the common reaction pathway proposed in the literature: the transmetalation process requires two additional steps. This modification can be attributed to the relative ability of the bis-hydrazone ligand, which can easily dissociate one of the N atoms directly coordinated to Pd catalyst (hemilabile behavior). As far as the stereochemistry of the reaction is concerned, calculations so far do not provide a clear explanation for the high enantioselectivities observed in the experiments. In summary, the theoretical results derived from this thesis have demonstrated that theoretical calculations are a very useful tool for elucidating and/or proposing reaction mechanisms for these type of processes.
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Munday, Rachel Hannah. "Vinyldimethylphenylsilanes as latent partners in cross-coupling reactions." Thesis, University of Nottingham, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.430546.

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Zhang, Liang. "Catalytic Conjunctive Cross-Coupling and Catalytic Diboration Reactions." Thesis, Boston College, 2017. http://hdl.handle.net/2345/bc-ir:107561.

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Thesis advisor: James P. Morken
This dissertation will present four main projects focused on stereoselective construction of borylated compounds as well as their applications in asymmetric syntheses. The first two projects describe the development of a catalytic conjunctive cross-coupling reaction. By merging three simple starting materials, an organolithium reagent, an organoboronate, and an organic electrophile, a synthetically valuable secondary boronate is furnished by the conjunctive cross-coupling in an efficient and enantioselective fashion. Next, this strategy is expanded to synthesize severely hindered tertiary boronates, a synthetic challenging but powerful building block to access a variety of quaternary stereocenters. The third project presents a platinum-catalyzed enantioselective diboration of alkenyl boronates to furnish a broad range of 1,1,2-tris(boronates) products. A deborylative alkylation of the 1,1,2-tris(boronates) leads to a variety of internal vicinal bis(boronates) with high diastereoselectivity. In the final chapter, a general and practical synthesis of alkenyl boronates via the boron-Wittig reaction is disclosed. Utilizing readily accessible geminal bis(boronates) and aldehydes, a broad range of disubstituted and trisubstituted alkenyl boronates are afforded with good yield and stereoselectivity
Thesis (PhD) — Boston College, 2017
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Parry, Paul Richard. "New pyridylboronic acids and their cross-coupling reactions." Thesis, Durham University, 2003. http://etheses.dur.ac.uk/3705/.

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The novel substituted pyridylboronic acids 2-bromo-5-pyridylboronic acid 92, 3-hromo-5- pyridylboronic acid 97, 2-chloro-5-pyridylboronic acid 103, 2-fluoro-5- pyridylboronic acid 108, 2-methoxy-5-pyridylboronic acid 123, 2-ethoxy-5- pyridylboronic acid 125, 2-medioxy-3-pyridylboronic acid 131, 3-bromo-6-methoxy-4- pyridylboronic acid 134, 3-chloro-6-methoxy-4-pyridylboronic acid 137 and 3-hromo-6- ethoxy-4-pyridylboronic acid 138 have been synthesised and shown to undergo palladium-catalysed Suzuki cross-coupling reactions with a vast variety of heteroaryl bromides to yield novel heteroarylpyridine derivatives.5-Formylfnran-2-boronic acid 170 has been synthesised and isolated and has been shown to undergo palladium-catalysed Suzuki cross-coupling reactions with a variety of heteroaryl bromides to yield novel heteroaryl substituted furyl derivatives. These derivatives have been shown to undergo efficient functionalisation by Wittig chemistry.
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Books on the topic "Cross Reactions"

1

Miyaura, Norio, ed. Cross-Coupling Reactions. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/3-540-45313-x.

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Lei, Aiwen, Wei Shi, Chao Liu, Wei Liu, Hua Zhang, and Chuan He. Oxidative Cross-Coupling Reactions. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2016. http://dx.doi.org/10.1002/9783527680986.

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Nishihara, Yasushi, ed. Applied Cross-Coupling Reactions. Berlin, Heidelberg: Springer Berlin Heidelberg, 2013. http://dx.doi.org/10.1007/978-3-642-32368-3.

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Diederich, François. Metal-catalyzed cross-coupling reactions. New York: Wiley-VCH, 1998.

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Evano, Gwilherm, and Nicolas Blanchard, eds. Copper-Mediated Cross-Coupling Reactions. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2013. http://dx.doi.org/10.1002/9781118690659.

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Diederich, François, and Peter J. Stang, eds. Metal-Catalyzed Cross-Coupling Reactions. Weinheim, Germany: Wiley-VCH Verlag GmbH, 1998. http://dx.doi.org/10.1002/9783527612222.

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de Meijere, Armin, Stefan Bräse, and Martin Oestreich, eds. Metal-Catalyzed Cross-Coupling Reactions and More. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2014. http://dx.doi.org/10.1002/9783527655588.

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Correa, Arkaitz, ed. Ni- and Fe-Based Cross-Coupling Reactions. Cham: Springer International Publishing, 2017. http://dx.doi.org/10.1007/978-3-319-49784-6.

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Lei, Aiwen, ed. Transition Metal Catalyzed Oxidative Cross-Coupling Reactions. Berlin, Heidelberg: Springer Berlin Heidelberg, 2019. http://dx.doi.org/10.1007/978-3-662-58104-9.

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Wolfe, J. P. (James Philip), 1943- and Larhed Mats, eds. Science of synthesis: Cross coupling and Heck-type reactions. Stuttgart: Georg Thieme Verlag KG, 2013.

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Book chapters on the topic "Cross Reactions"

1

Paetz gen. Schieck, Hans. "Cross Sections." In Nuclear Reactions, 61–75. Berlin, Heidelberg: Springer Berlin Heidelberg, 2014. http://dx.doi.org/10.1007/978-3-642-53986-2_4.

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Paetz gen. Schieck, Hans. "Classical Cross Section." In Nuclear Reactions, 13–38. Berlin, Heidelberg: Springer Berlin Heidelberg, 2014. http://dx.doi.org/10.1007/978-3-642-53986-2_2.

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Paetz gen. Schieck, Hans. "Unpolarized Cross Sections." In Nuclear Reactions, 131–43. Berlin, Heidelberg: Springer Berlin Heidelberg, 2014. http://dx.doi.org/10.1007/978-3-642-53986-2_8.

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Li, Jie Jack. "Hiyama cross-coupling reaction." In Name Reactions, 165–66. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_132.

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Li, Jie Jack. "Kumada cross-coupling reaction." In Name Reactions, 207–8. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_160.

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Li, Jie Jack. "Negishi cross-coupling reaction." In Name Reactions, 254. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_200.

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Li, Jie Jack. "Hiyama cross-coupling reaction." In Name Reactions, 288–89. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_126.

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Li, Jie Jack. "Kumada cross-coupling reaction." In Name Reactions, 325–27. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_144.

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Li, Jie Jack. "Negishi cross-coupling reaction." In Name Reactions, 389–90. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_177.

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Li, Jie Jack. "Hiyama cross-coupling reaction." In Name Reactions, 316–17. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_134.

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Conference papers on the topic "Cross Reactions"

1

Itoh, O., H. Utsunomiya, H. Akimune, T. Yamagata, T. Kondo, M. Kamata, H. Toyokawa, et al. "PHOTONEUTRON CROSS SECTIONS FOR Au." In FRONTIERS IN NUCLEAR STRUCTURE, ASTROPHYSICS, AND REACTIONS: FINUSTAR 3. AIP, 2011. http://dx.doi.org/10.1063/1.3628413.

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Marrone, S. "Implications of 151Sm(n,γ) Cross Section at n_TOF." In FRONTIERS IN NUCLEAR STRUCTURE, ASTROPHYSICS, AND REACTIONS - FINUSTAR. AIP, 2006. http://dx.doi.org/10.1063/1.2200996.

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Terlizzi, R. "Measurement of 139La(n,γ) Cross Section at n_TOF." In FRONTIERS IN NUCLEAR STRUCTURE, ASTROPHYSICS, AND REACTIONS - FINUSTAR. AIP, 2006. http://dx.doi.org/10.1063/1.2201012.

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Hilaire, S., S. Goriely, A. J. Koning, M. Girod, Paraskevi Demetriou, Rauno Julin, and Sotirios Harissopulos. "Nuclear ingredients for cross section calculation of exotic nuclei." In FRONTIERS IN NUCLEAR STRUCTURE, ASTROPHYSICS, AND REACTIONS: FINUSTAR 3. AIP, 2011. http://dx.doi.org/10.1063/1.3628383.

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Lemut, A. "Low energy underground study of 14N(p,γ)15O cross section." In FRONTIERS IN NUCLEAR STRUCTURE, ASTROPHYSICS, AND REACTIONS - FINUSTAR. AIP, 2006. http://dx.doi.org/10.1063/1.2200958.

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Belgaid, M. "Systematic Studies of (n,p) Reaction Cross Sections for 14.5 MeV Neutrons." In FRONTIERS IN NUCLEAR STRUCTURE, ASTROPHYSICS, AND REACTIONS - FINUSTAR. AIP, 2006. http://dx.doi.org/10.1063/1.2200962.

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LI, JING, SAKAMOTO JUMPEI, HIROKI WIZUMI, YUE HUANG, NAOKI KISHIMOTO, YUTAKA OYA, and TOMONAGA OKABE. "From Addition Reactions to Cross-Linked Network Formation." In American Society for Composites 2018. Lancaster, PA: DEStech Publications, Inc., 2018. http://dx.doi.org/10.12783/asc33/25964.

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Čapek, Petr, Miroslav Otmar, Milena Masojídková, and Antonín Holý. "Cross-coupling reactions of 2,6-dichloro-9-deazapurine." In XIIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2002. http://dx.doi.org/10.1135/css200205304.

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Chasioti, V. C., P. C. Divari, T. S. Kosmas, Osvaldo Civitarese, Ivan Stekl, and Jouni Suhonen. "Realistic Calculations for Neutrino-Nucleus Reactions Cross sections." In WORKSHOP ON CALCULATION OF DOUBLE-BETA-DECAY MATRIX ELEMENTS (MEDEX'07). AIP, 2007. http://dx.doi.org/10.1063/1.2805102.

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Chasioti, V. C., T. S. Kosmas, P. C. Divari, Livius Trache, and Sabin Stoica. "Realistic Calculations for Neutrino-Nucleus Reactions Cross sections." In EXOTIC NUCLEI AND NUCLEAR/PARTICLE ASTROPHYSICS (II): Proceedings of the Carpathian Summer School of Physics 2007. AIP, 2008. http://dx.doi.org/10.1063/1.2870371.

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Reports on the topic "Cross Reactions"

1

Younes, W. General Constraints on Cross Sections Deduced from Surrogate Reactions. Office of Scientific and Technical Information (OSTI), August 2003. http://dx.doi.org/10.2172/15004554.

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2

Houston, P. L. Studies of combustion reactions at the state-resolved differential cross section level. Office of Scientific and Technical Information (OSTI), March 1992. http://dx.doi.org/10.2172/7206981.

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3

Rutherford, D. A. Theoretical and experimental cross sections for neutron reactions on /sup 64/Zinc. Office of Scientific and Technical Information (OSTI), March 1988. http://dx.doi.org/10.2172/5544684.

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Penionzhkevich, Yu E., Yu G. Sobolev, V. V. Samarin, and M. A. Naumenko. Study of enhancement of total cross sections of reactions with 6He, 6,9Li nuclei. PHYSICAL-TECHNICAL SOCIETY OF KAZAKHSTAN, November 2017. http://dx.doi.org/10.29317/ejpfm.2017010102.

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Peerey, L. Cross-linked metalloproteins: Novel systems for the study of intraprotein electron-transfer reactions. Office of Scientific and Technical Information (OSTI), January 1990. http://dx.doi.org/10.2172/7118554.

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Zhao, Z. X., C. Y. Fu, and D. C. Larson. Calculated cross sections for neutron induced reactions on sup 19 F and uncertainties of parameters. Office of Scientific and Technical Information (OSTI), September 1990. http://dx.doi.org/10.2172/6383176.

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7

Fotiadis, Nikolaos, Matthew James Devlin, Ronald Owen Nelson, and James Carroll. Partial gamma-ray cross section measurements in 109Ag(n, x n y p gamma) reactions. Office of Scientific and Technical Information (OSTI), June 2015. http://dx.doi.org/10.2172/1183402.

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8

Hoffman, D. C., and M. M. Hoffman. Calculation of cross sections for binary reactions between heavy ion projectiles and heavy actinide targets. Office of Scientific and Technical Information (OSTI), November 1990. http://dx.doi.org/10.2172/5927588.

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9

Gorton, O., and J. Escher. Cross Sections for Neutron-Induced Reactions from Surrogate Data: Assessing the Use of the Weisskopf-Ewing Approximation for (n,n') and (n,2n) Reactions. Office of Scientific and Technical Information (OSTI), September 2020. http://dx.doi.org/10.2172/1668500.

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10

Blann, M., and T. T. Komoto. Cross sections and differential spectra for reactions of 2-20 MeV neutrons of /sup 27/Al. Office of Scientific and Technical Information (OSTI), January 1988. http://dx.doi.org/10.2172/5500429.

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