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Showing 1 to 20 of 26 for “"aryl chlorides"”.
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Synthesis of indoles via palladium-catalyzed annulation of aryl chlorides and internal alkynes
… in most cases. Alkynes with alkyl, aryl, alkenyl, and trialkylsilyl substituents are compatible with this methodology.
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Application of a palladium/tri-tert-butylphosphine catalyst system towards mild and general methods for carbon-carbon bond formation
… We have concentrated on the utilization of aryl chlorides as substrates due to their lower cost and greater availability compared to traditionally employed aryl bromides, iodides, and triflates. The Suzuki reaction was the first reaction that we investigated, and we were able to develop a …
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Late transition metal catalyzed C-N and C-C bond forming reactions
… methods for the palladium-catalyzed amination of aryl halides are described. Key to these is the development of new catalysts and reaction conditions for these transformations. Initially, P(o-tol)3 ligated palladium catalysts were investigated but gave way to systems that used chelating phosphine …
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Development and Applications of Pd Catalysts for C-N Cross-Coupling Reactions
… Pd(0) catalyst from Pd(OAc) 2, water, and biarylphosphine ligands has been developed. This protocol generates a catalyst system, which exhibits excellent reactivity and efficiency in the coupling of a variety of amides and anilines with aryl chlorides. Chapter 2 A new class of one-component …
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Development and Mechanistic Investigation of the Palladium-Catalyzed Alpha-Arylation of Aldehydes and N-Arylation of Ammonia
… the palladium-catalyzed coupling of ammonia with aryl halides and sulfonates was also developed. The catalyst generated from Pd[P(o-tol)3]2 and the alkylbisphophine CyPF-t-Bu is a highly active and selective catalyst for the coupling of ammonia with aryl chlorides, bromides, iodides, and …
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Carbon-trifluoromethyl bond forming reactions and palladium-catalyzed cyanation of (hetero)aryl halides
… the first system for the trifluoromethylation of aryl chlorides. Chapter 2 A method for the oxidative trifluoromethylation of (hetero)aryl boronic acids is reported. Bench top setup and visual reaction monitoring makes this process particularly well suited to medicinal and academic chemists. Fast …
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Palladium-catalyzed C-N and C-O cross-coupling reactions
… a general method for the of the Pd-catalyzed N-arylation of hindered [alpha],[alpha],[alpha]-trisubstituted primary amines. The reaction utilized catalysts based on two biaryl phosphine ligands, which were developed via kinetics-based mechanistic analysis and rational design. These studies led …
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The versatility and utilization of phosphorus based compounds in classic carbon-carbon bond forming and esterification reactions
… catalyzed Suzuki cross-coupling reaction of aryl halides, including aryl chlorides, under mild conditions. The cross-coupling reactions were found to proceed in THPC containing small amounts ofwater and toluene (single phase) using potassium phosphate and 1% Pd2(dba)3'CHCI3. Variously …
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Development and mechanistic investigation of the palladium-catalyzed α-arylation of aldehydes and N-arylation of ammonia
A general method for the palladium-catalyzed α-arylation of aldehydes was developed to couple linear and branched aldehydes with electron-poor and electron-rich bromo- and chloroarenes in high yields. Catalysts generated from allylpalladium chloride (APC) and 1,1’-diphenylphosphinoferrocene (DPPF) …
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Synthesis, Activation and Catalytic Activity of N-Heterocyclic Carbene Bearing Palladium Catalysts
… and related (catalytic dehalogenation, £-ketone arylation) reactions is also discussed. A comparison of the activity of a variety of (NHC)Pd complexes as pre-catalysts for cross-coupling reactions was carried out. The results indicate that the activation of those pre-catalysts, leading to the …
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Development of new catalytic transformations and reagents for the construction of C-N and C-S bonds
Chapter 1. Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas. An efficient method for palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate is reported. The protocol allows for the …
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The development of palladium-catalysts for organic synthesis
Chapter 1. Suzuki-Miyaura coupling reactions of aryl and heteroaryl halides with aryl-, heteroaryl and vinyl boronic acids proceed in very good to excellent yield with the use of 2-(2',6'-dimethoxybiphenyl)-dicyclohexylphosphine, SPhos. Additionally, a comparison of the reactions with SPhos and …
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Development of Palladium(0)-Catalyzed Suzuki Cross-Coupling Polymerizations
… Suzuki cross-coupling polymerization of aryl dibromides with aryldiboronic acids at room temperature. Based on our understanding of Pd(0)-catalyzed Suzuki cross-coupling polymerization process, I figured out the amount of the base used, and the solubility of the polymers were the mainly …
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Modifications to the Suzuki reaction and mechanistic insights on the NBS mediated cleavage of benzylidene acetals /
… catalyzed Suzuki cross-coupling reaction of aryl halides, including aryl chlorides, under mild conditions. The cross-coupling reactions were found to proceed in THPC containing small amounts of water and toluene using potassium phosphate and 1% Pd2(dba)3. Variously substituted iodobenzenes, …
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The nickel-catalyzed Mizoroki-Heck reaction : high regioselectivity in Olefin migratory insertion and photoredox-enabled indoline formation
… (>/=19:1 in all cases) over a wide range of aryl electrophiles and aliphatic olefins. A bidentate ligand with a suitable bite angle and steric profile was key to obtaining high branched/linear selectivity, while the appropriate base suppressed alkene isomerization of the product. Though aryl …
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Catalytic enantioselective synthesis of oxindoles and benzofuranones bearing a quaternary stereocenter and reactions of palladium bisphosphine complexes relevant to catalytic C-C bond formation
… catalyst than Pd(PCy₃)₂ for the Heck coupling of aryl chlorides. Finally, Part III describes preliminary work on a palladium-hydride catalyzed isomerization of allylic alcohols as well as initial attempts to study the mechanism of nickel-catalyzed cross-couplings of secondary alkyl-electrophiles.
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Palladium-catalyzed reactions of ammonia, carbon monoxide, and cyanide
The reductive eliminations of primary arylamines from a series of bisphosphine-ligated arylpalladium(II) parent amido complexes countered several established trends. In contrast to arylamido and alkylamido complexes of the aromatic bisphosphines DPPF and BINAP, parent amido complexes did not form …
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Recent advances in palladium-catalyzed carbon-carbon and carbon-boron bond forming processes
… Suzuki-Miyaura cross-coupling reaction of heteroaryl boronic acids and esters has been developed. This method allows for the preparation of a wide variety of heterobiaryls in good to excellent yields and displays a high level of activity for the coupling of heteroaryl chlorides as well as …
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Iterative cross-coupling with MIDA boronates
… cross-coupling reactions with deactivated aryl chlorides. Enabled by these collective discoveries, and towards the goal of a simple and accessible approach to small molecule synthesis, a machine with the capacity to perform fully automated ICC syntheses was developed and was employed in the …
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The Modified Stereospecific Stille Reaction: Palladium-Catalyzed Cross-Coupling Reactions Involving Secondary and Tertiary Alkyl Carbastannatranes
… of secondary alkyl organotin reagents with aryl chlorides, bromides, iodides and triflates. The reaction proceeds with minimal isomerization of the secondary alkyl organometallic tin nucleophile, and tolerates a wide range of functional groups with absolute configuration. In the third …
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