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Relevant bibliographies by topics / C-H bonds functionalisation

Academic literature on the topic 'C-H bonds functionalisation'

Author: Grafiati

Published: 10 December 2022

Last updated: 29 January 2023

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Dissertations / Theses
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Journal articles on the topic "C-H bonds functionalisation"

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Banerjee, Arghya, Satavisha Sarkar, and Bhisma K. Patel. "C–H functionalisation of cycloalkanes." Organic & Biomolecular Chemistry 15, no. 3 (2017): 505–30. http://dx.doi.org/10.1039/c6ob01975g.

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Prakash, Gaurav, Nilanjan Paul, Gwyndaf A. Oliver, Daniel B. Werz, and Debabrata Maiti. "C–H deuteration of organic compounds and potential drug candidates." Chemical Society Reviews 51, no. 8 (2022): 3123–63. http://dx.doi.org/10.1039/d0cs01496f.

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This review summarises deuteration methods of various organic motifs containing C(sp2)−H and C(sp3)−H bonds utilizing C−H bond functionalisation as a key step along with a variety of catalysts, and exemplifies their biological relevance.

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Patrick, Scott R., Ine I. F. Boogaerts, Sylvain Gaillard, Alexandra M. Z. Slawin, and Steven P. Nolan. "The role of silver additives in gold-mediated C–H functionalisation." Beilstein Journal of Organic Chemistry 7 (July 1, 2011): 892–96. http://dx.doi.org/10.3762/bjoc.7.102.

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The role of silver additives is examined in the context of gold-mediated functionalisation of aromatic C–H bonds. Doubt is cast on the commonly cited route of halide abstraction from gold and evidence of substrate activation is given.

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Che, Chi-Ming, Vanessa Kar-Yan Lo, Cong-Ying Zhou, and Jie-Sheng Huang. "Selective functionalisation of saturated C–H bonds with metalloporphyrin catalysts." Chemical Society Reviews 40, no. 4 (2011): 1950. http://dx.doi.org/10.1039/c0cs00142b.

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Crowe, Charlotte, Samuel Molyneux, Sunil V. Sharma, Ying Zhang, Danai S. Gkotsi, Helen Connaris, and Rebecca J. M. Goss. "Halogenases: a palette of emerging opportunities for synthetic biology–synthetic chemistry and C–H functionalisation." Chemical Society Reviews 50, no. 17 (2021): 9443–81. http://dx.doi.org/10.1039/d0cs01551b.

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Vellakkaran, Mari, Jagadish Das, Sourajit Bera, and Debasis Banerjee. "Nickel-catalysed alkylation of C(sp3)–H bonds with alcohols: direct access to functionalised N-heteroaromatics." Chemical Communications 54, no. 87 (2018): 12369–72. http://dx.doi.org/10.1039/c8cc06370b.

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Gulzar, Naeem, Bertrand Schweitzer-Chaput, and Martin Klussmann. "Oxidative coupling reactions for the functionalisation of C–H bonds using oxygen." Catalysis Science & Technology 4, no. 9 (June 16, 2014): 2778. http://dx.doi.org/10.1039/c4cy00544a.

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Shaikh, Mohammed Umar M., Sulochana S. Mudaliar, and Kishor H. Chikhalia. "An efficient alkynylation of 4-thiazolidinone with terminal alkyne under C–H functionalisation." RSC Advances 6, no. 56 (2016): 50780–85. http://dx.doi.org/10.1039/c6ra05015h.

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St John-Campbell, Sahra, and James A. Bull. "Transient imines as ‘next generation’ directing groups for the catalytic functionalisation of C–H bonds in a single operation." Organic & Biomolecular Chemistry 16, no. 25 (2018): 4582–95. http://dx.doi.org/10.1039/c8ob00926k.

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This review describes recent developments in the use of catalytic transient directing groups, through imine linkages, which in combination with transition metal catalysts provide streamlined C–H functionalisation processes.

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Gulzar, Naeem, Bertrand Schweitzer-Chaput, and Martin Klussmann. "ChemInform Abstract: Oxidative Coupling Reactions for the Functionalisation of C-H Bonds Using Oxygen." ChemInform 45, no. 41 (September 25, 2014): no. http://dx.doi.org/10.1002/chin.201441235.

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Dissertations / Theses on the topic "C-H bonds functionalisation"

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Davis, Holly. "Harnessing non-covalent interactions to control regioselectivity in the functionalisation of arene C-H bonds." Thesis, University of Cambridge, 2018. https://www.repository.cam.ac.uk/handle/1810/277900.

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Yahaya, N. P. "Cyclometallation at Pd, Mn and Co : functionalisation of C-H and C≡C bonds involving cyclisation, rearrangement and isomerisation processes." Thesis, University of York, 2016. http://etheses.whiterose.ac.uk/12566/.

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This thesis describes cyclometallation at Pd, Mn and Co: functionalisation of C H and C≡C bonds involving cyclisation, rearrangement and isomerisation processes. The use of NaNO2/NaNO3 as an oxidant in oxidative Pd-catalyzed processes has recently been reported as a complementary co-catalyst to other common oxidants (e.g. CuII/AgI salts). In view of this (Chapter two) the synthesis of a series of palladacyclic complexes containing a C^N ligand backbone, and the geometry and linkage isomerism at NO2 Pd, has been studied. The geometry about the Pd(II) centre shows the crucial role played by bulky ligands in creating hindrance and affecting phosphine dissociation. Mn-catalysed C-H bond activation is a powerful strategy for the functionalisation of organic compounds containing metal-directing groups. Chapter three of this thesis reports the characterisation of a highly reactive 7-membered MnI species which acts as anvil point between protonation and reductive elimination to deliver alkenylated and/or pyridinium products respectively. Both processes are exemplified through the reactions of a substrate containing a 2-pyridyl directing group and electron-deficient 2-pyrone motif at MnI, where C-H bond activation occurs regioselectively at C3 within the 2-pyrone. An unprecedented regioselective Diels-Alder reaction also occurs on both the pyridine and 2-pyrone ring systems. These findings provide a unique insight into MnI-mediated C-H bond activation processes, especially how relatively minor changes in substrate structure influence the product distribution. The study shows that MnI-based metallocycles warrant further study more generally in organic and organometallic chemistry The intermolecular Pauson-Khand (PK) reactions of sterically comparable (2-pyridylethynyl)-heteroaromatic compounds with norbornene, mediated by Co2(CO)8 to give cyclopentenone products, were examined in Chapter four of this thesis. The π-deficient heteroaromatic substrate, 2-pyrone, favoured the -position while the π-rich heteroaromatics such as 2-thiophene favour the β-position. The position of the nitrogen in pyridyl-containing alkyne substrates also affects the regiochemical outcome of the PK reaction. A 2-pyridyl alkyne, possessing a proximal nitrogen atom, influences the regioselectivity relative to a 4-pyridyl variant, quite dramatically, favouring the β-position in the newly formed cyclopentenone ring. Overall, the type of heteroaromatic group greatly influences PK regioselectivity. The PK cycloadducts undergo a 6π-electrocyclisation–oxidative aromatisation reaction in the presence of light, which is promoted by a LED UV-light controlled system, affording benzo[h]indeno[1,2-f]isochromene type products.

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Truscott, Fiona Rosemary. "Transition metal catalysed C-C bond formation via C-H functionalisation." Thesis, University of Oxford, 2012. http://ora.ox.ac.uk/objects/uuid:6a1ef296-8d63-470d-96bd-3e01a887c81f.

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The functionalisation of C-H bonds has been widely studied in organic synthesis. This work presents the results of investigation into two areas of current research, copper-catalysed aromatic C-H functionalisation and rhodium-catalysed hydroacylation. Chapter 1 presents the development of palladium- and copper-catalysed aromatic C-H functionalisation with particular attention paid to regiocontrol. Chapter 2 describes the development of copper-catalysed cross-coupling of perfluorinated arenes and alkenyl halides along with efforts to expand this methodology to a more general reaction. In Chapter 3 the development of chelation-controlled rhodium-catalysed hydroacylation is discussed. Chapter 4 outlines the utilisation of amino acid derived N-methylthiomethyl aldehydes in rhodium-catalysed hydroacylation methodology.

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Teskey, Christopher. "Strategic use of transition metals for selective C-H bond functionalisation." Thesis, University of Manchester, 2016. https://www.research.manchester.ac.uk/portal/en/theses/strategic-use-of-transition-metals-for-selective-ch-bond-functionalisation(496828e4-75db-428e-afb5-0138d55c3258).html.

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The ability to selectively react C-H bonds in organic molecules is a field within synthetic chemistry that has grown substantively in the last few decades. The interest in this area emanates from the desire to maximise atom economy: this approach obviates the need for pre-functionalised starting materials and stoichiometric organometallic reagents. However, organic molecules typically contain many different C-H bonds with little difference in bond energy which can make selective functionalisation difficult to achieve. Herein is described how ruthenium catalysis was shown to effect meta-bromination on substituted 2-phenylpyridines. This novel procedure shows a marked contrast to other transition metal catalysed bromination procedures which are selective for the ortho-position of the phenyl ring. It was shown that this methodology was compatible with more traditional palladium catalysed chemistries (Suzuki-Miyaura and Heck reactions) in the same pot which enabled the development of procedures for one-pot meta-arylation and meta-alkenylation. Mechanistic postulation on the meta-bromination procedure led to the discovery of several interesting new meta-selective C-H functionalisation reactions with ruthenium catalysis. The early investigations, together with the challenges faced, are described. Subsequent investigations into other halogenating agents with ruthenium catalysis showed that iodine monochloride gave interesting results, with switchable chemoselectivity through variance of catalyst giving ortho-chlorinated or ortho-iodinated products. Also presented is a copper mediated coupling of electron rich arenes and toluene-like molecules to give (halo)diarylmethanes. This formal cross dehydrogenative coupling strategy tolerates a wide range of coupling partners for both the electron rich arene and the tolyl-component. Mechanistic studies suggest that the reaction proceeds via a copper mediated coupling of an in situ generated aryl bromide with a benzylic radical species.

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Williams, Thomas. "Understanding C-H bond functionalisation at heterocycles and biomolecules : a synthetic and mechanistic study." Thesis, University of York, 2013. http://etheses.whiterose.ac.uk/4133/.

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The Pd-, Cu- and Pd/Cu-mediated direct functionalisation of C2-H bonds at 1,3-X,N-heterocycles (where X = S, O, N) and indole-containing biomolecules has been investigated. Such processes are useful in the synthesis and labeling of complex molecules, and represent an improvement on traditional Pd-mediated cross-coupling. A study of the mechanism of C2-H bond functionalisation of 1,3-X,N-heterocycles (specifically benzimidazole, benzothiazole and benzoxazole) with Pd/Cu catalyst systems has indicated a key role for Pd0 nanoparticles. Nanoparticles have been demonstrated to form in situ when molecular PdII pre-catalysts are employed, and have been characterized by transmission electron microscopy (TEM). The catalytic activity of these nanoparticles has been shown to vary with reaction environment (e.g. the use of different reaction vessels). Pre-synthesised, well-defined Pd0 nanoparticles supported on polyvinylpyrolidone (PVP) are effective catalysts for these processes and increase reaction reliability. It is proposed that Cu N-heterocarbene(NHC) intermediates play a key role in these processes. A model system {(1,3-dibenzyl)benzoimidazolylidenecopper(I) bromide} has been synthesised using an electrochemical method. The reaction of this model with PhI within and without the presence of PdII results in arylated product. Whilst conducting these studies, the novel compound bis{(1,3-dibenzyl)benzimidazolium}dicopper(I)tetrabromide was isolated. The C-H bond functionalisation of benzoxazole with a Pd/(1,10-phenanthroline)catalyst and PhI(OAc)2 aryl source has been studied in detail. Pd0 nanoparticles have isolated and characterized from this reaction. It has also been demonstrated that PhI(OAc)2 rapidly degrades to PhI under the reaction conditions. The indole-based amino acid tryptophan is fluorescent, and modifying this fluorescence is of interest. A mild and selective C2-H bond functionalisation reaction for this amino acid has been developed, both as a single residue and within peptides. NMR spectroscopy, ReactIR® and other techniques have been used to build up a mechanistic picture of this reaction, with is proposed to proceed via a Pd0/II manifold.

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Beck, Elizabeth Mary. "New strategies for chemical synthesis : metal-catalyzed C-H bond functionalisation for complex molecule synthesis." Thesis, University of Cambridge, 2008. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.596508.

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A new method for oxidative palladium (II) catalyzed direct C-H bond alkenylation of pyrroles has been developed, wherein the position of functionalisation can be influenced using a steric and electronic control strategy. Despite the sensitivity of pyrroles towards oxidation and polymerization, the reaction works well for a range of substrates and can proceed under extremely facile and mild conditions using air, oxygen gas or t-BuOOBz as an oxidising system for the palladium. The synthesis of (±)-rhazinicine 1 demonstrates how iterative application of such C-H bond functionalization tactics can positively influence strategic planning in complex molecule assembly. The key motifs are directly installed from a simple pyrrole nucleus using two site-selective catalytic C-H functionalization transformations. The utility of functionalized pyrroles in the synthesis of elaborated pyrrolidines was then investigated through a transannular cyclisation cascade strategy to access (±)-aspidospermindine 3 from the natural product (±)-rhazinilam 2.

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Reay, Alan. "Development of Pd-catalysed C–H bond functionalisation methodologies for the accession of molecular complexity." Thesis, University of York, 2016. http://etheses.whiterose.ac.uk/13161/.

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This thesis describes the development of novel Pd-catalysed C–H bond functionalisation methodologies, with a view towards their application in sustainable chemical synthesis. The basis of this project focuses on the need for more efficient utilisation of precious metal catalysts, such as Pd, achieved by mechanistic understanding of the role of heterogeneous Pd nanoparticles (PdNPs) in such chemistry. An overview of observations from Pd-catalysed cross-coupling and C–H bond functionalisation chemistry is given initially, focusing on the mechanistic dichotomy between observed homogeneous and heterogeneous catalytic manifolds in these fields. The generation of potentially harmful stoichiometric byproducts in direct arylation methodologies is also examined for two classes of commonly-used electrophilic arylating agents, aryliodonium and aryldiazonium salts (Chapter 1). The synthetic utility of C–H bond functionalisation chemistry has been exemplified through the development of complementary conditions for the direct arylation of the amino acid tryptophan (I) to form highly fluorescent 2-aryltryptophans (II), all of which have been evaluated using several key mass-based green metrics (Chapter 2). These conditions have also been shown to be effective for the functionalisation of tryptophan-containing peptides. Initial rates kinetic analysis of the activity of several homogeneous and heterogeneous Pd catalysts in other direct arylation chemistry has highlighted remarkable similarities between apparently distinct catalysts, which suggests the formation of a comparable active catalyst phase. Heterogeneous Pd sources have also been successfully applied to the selective functionalisation of several biomolecules (Chapter 3). The final part of this thesis describes fundamental studies on the nature of the ubiquitous Pd0 catalyst Pd2(dba)3. The major and minor isomers of this catalyst were characterised both in solution and in the solid state, which revealed that dynamic exchange between these species and free ligand varies significantly as a function of temperature. Crucially, this catalyst has also been shown by NMR and MS studies to be a source of catalytically competent PdNPs under commonly-found experimental conditions (Chapter 4).

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Chen, Lu. "Palladium-catalysed C-C bond construction in virtue of C-H functionalisation : direct arylation of heteroaromatics tolerant to reactive functional groups." Thesis, Rennes 1, 2013. http://www.theses.fr/2013REN1S011.

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Durant ma thèse, j'ai recherché les conditions pour l'activation / fonctionnalisation de liaisons C-H pour la construction de bi(hétéro)aryles tolérant des groupement fonctionnels réactifs tels que des silyles, des alcènes, des esters ou encore des amides. Par rapport aux protocoles de couplage classiques tels que les réactions de Suzuki, Stille ou Negishi, la fonctionalisation de liaisons C-H fournit des procédures moins coûteuses et plus écologiques si elle tolère des groupements utiles en synthèse. D'abord, nous avons observé que les thiophènes substitués par des silyles en C2 peuvent être arylés avec des bromures d'aryle sans désilylation en présence du précatalyseur Pd(OAc)2/dppb. Les produits de couplage sont obtenus avec de bons rendements et avec inhibition de la réaction de désilylation. Ensuite, nous avons démontré que le système Pd(OAc)2/KOAc sans ligand phosphine, favorise l'arylation directe des hétéroaromatiques et inhibe la réaction de type Heck avec des thiophenes substitués par des alcènes substituées sur les carbones 2 ou 3. Ensuite, nous avons démontré que les fonctions esters sur les hétéroaromatiques peuvent être avantageusement utilisées comme groupements protecteurs, permettant l'arylation directe d'hétéroaromatiques sur le carbone C5. Enfin, l'heteroarylation directe de 2- ou 4-bromobenzamides avec des hétéroarènes catalysée au palladium a été étudiée. En présence de KOAc comme base, aucune formation de liaisons C-C ou C-N par couplage de deux bromobenzamides n'a été observée
During my thesis, I focused on condition for the activation / functionalisation of C-H bonds for the construction of biaryl derivatives tolerant to the reactive functional groups such as silyl, alkenes, esters or amides. Compared to classic cross-coupling protocols (Suzuki, Stille or Negishi), C-H bond functionalisation provides a costly effective and environmentally attractive procedures. At first, we observed that the silyl-substituted thiophenes can be directly arylated with aryl bromides without desilylation, using the simple Pd(OAc)2/dppb precatalyst for both conversion and desilylation inhibition. Then, we have demonstrated that the Pd(OAc)2/KOAc catalyst system without phosphine ligand, even using as few as 0.1 mol% of Pd catalyst, promotes the direct arylation of heteroaromatics and inhibits the Heck type reaction with 1,2-disubstituted alkenes. In addition, we demonstrated that easily accessible esters on heteroaromatics can be advantageously employed as blocking groups in the course of the direct arylation of several heteroaromatic derivatives. Finally, the palladium-catalyzed direct heteroarylation of 2- or 4-bromobenzamide with heteroarenes was studied. In the presence of KOAc as the base, no formation of C-N or C-C bonds by coupling of two bromobenzamide was observed

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Haffemayer, Benjamin. "Development of novel amine-directed Pd(II)-catalysed sp2 and sp3 C-H bond functionalisation processes." Thesis, University of Cambridge, 2013. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.607792.

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Platt, George. "Mechanistic investigation into the Pd-catalysed C–H bond functionalisation of fluoroarenes : reaction kinetics and intermediate characterisation." Thesis, University of York, 2016. http://etheses.whiterose.ac.uk/17253/.

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The project aimed to reveal mechanistic details of the Pd-catalysed direct arylation reaction involving fluoroarenes. Direct arylation methodologies have rapidly developed over the last decade as cost-effective, eco-friendly and sustainable alternatives to cross-coupling reactions. Fluoroarenes are attractive substrates due to the fluorine-substitution effect as well as the ability to control the regioselectivity of C–H bond activation by the ortho-fluorine effect. Understanding the reaction mechanisms are crucial for making improvements to the C–H bond functionalisation field and provides access to unique reactivities. A literature reaction condition and the setup for the direct arylation reaction of iodoarene with fluoroarene was tailored for monitoring the progress by in situ FT-IR spectroscopic analysis. Kinetic information regarding the relationship between the reaction rate and factors such as concentrations, temperature, C–H bond strength and the electronic properties of the substrates were established. The catalytically relevant species were identified by in situ NMR spectroscopy, and ex situ MS. The reactivities of these species were confirmed by stoichiometric reactions and the ability to act as a catalyst.

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Book chapters on the topic "C-H bonds functionalisation"

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Bruneau, Christian, and Pierre H. Dixneuf. "Ruthenium(II)-Catalysed Functionalisation of C–H Bonds with Alkenes: Alkenylation versus Alkylation." In C-H Bond Activation and Catalytic Functionalization I, 137–88. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/3418_2015_134.

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Bruneau, Christian, and Pierre H. Dixneuf. "Erratum to: Ruthenium(II)-Catalysed Functionalisation of C–H Bonds with Alkenes: Alkenylation versus Alkylation." In C-H Bond Activation and Catalytic Functionalization I, 259–60. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/3418_2015_150.

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Haber, Jerzy. "Theoretical Basis of the Activation of C-H Bond." In Catalytic Activation and Functionalisation of Light Alkanes, 157–87. Dordrecht: Springer Netherlands, 1998. http://dx.doi.org/10.1007/978-94-017-0982-8_7.

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Carr, Kevin J. T., Stuart A. Macgregor, and Claire L. McMullin. "Computational Studies on Heteroatom-Assisted C–H Activation and Functionalisation at Group 8 and 9 Metal Centres." In C-H Bond Activation and Catalytic Functionalization I, 53–76. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/3418_2015_125.

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