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Showing 1 to 13 of 13 for “"cyanation"”.
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Electrophilic Cyanation of Alkenyl Tosylates, Ketones and Amines using Disubstituted Malononitriles
… disubstituted malononitriles as electrophilic cyanation reagents. These approaches may be of interest to workers attempting to access compounds of those types. Chapter 1 provides a brief overview of the thesis topics and compares nucleophilic to electrophilic cyanation. Chapter 2 describes a …
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Carbon-trifluoromethyl bond forming reactions and palladium-catalyzed cyanation of (hetero)aryl halides
… efficient system for the palladium-catalyzed cyanation of (hetero)aryl halides is disclosed. By employing palladacycle precatalysts, cyanide binding during catalyst formation is minimized, allowing for low catalyst loadings even with unactivated aryl chlorides. The method utilizes a non-toxic …
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Electrophilic C(sp²)–H Cyanation with Inorganic Cyanate (OCN⁻) by Pᴵᴵᴵ/Pⱽ=O-Catalyzed Phase Transfer Activation
A catalytic method for the direct electrophilic cyanation of C(sp²)–H nucleophiles with sodium cyanate (NaOCN) is reported. Mechanistic experiments show that under solid-liquid phase transfer, an inorganic cyanate is activated by halide displacement on a halophosphonium. Redox catalysis is enabled …
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Iridium-catalyzed borylation of aromatic and aliphatic C-H bonds: methodology and mechanism
A method to conduct the one-pot, meta cyanation of arenes by iridium-catalyzed C-H borylation and copper-mediated cyanation of the resulting arylboronate esters is described in Chapter 2. This process relies on a previously unknown method to conduct the cyanation of arylboronic esters, and …
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Part 1. Diaziridinium Ions: First Reported Synthesis and Reactivity Studies. Part 2. Tropylium Ion Mediated alpha-Cyanation of Amines. Part 3. Multicatalytic Synthesis of Complex Tetrahydrofurans
The first synthesis and full characterization of a new functionality, called the diaziridinium ion, is reported. The original synthetic intent behind its design was to explore its potential use as a non-metal based N-transfer reagent. During this study, we have uncovered a practical rearrangement …
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New reactivity and selectivity in transition metal-catalyzed C-C and C-N bond forming processes
… Chapter 5. Copper-Catalyzed ortho C-H Cyanation of Vinylarenes A copper-catalyzed regioselective ortho C-H cyanation of vinylarenes has been developed. This method provides an effective means for the selective functionalization of vinylarene derivatives. A copper-catalyzed cyanative …
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Synthesis and functionalization of novel meso-substituted tetrabenzotriazaporphyrins
… bromination and Rosenmund von Braun cyanation reaction in the last step. An alternative route towards the formation of the phthalonitriles was used in order to synthesise alternative target phthalonitriles in good yield; the method employed Kumada cross-coupling reaction using …
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Developments in Nickel-catalyzed Transfer Hydrocyanation Reactions and Novel Skeletal Editing Strategies through Nitrogen Atom Insertion
… the introduction of nitrile groups by hydrocyanation reactions that allow the formal addition of H–CN across unsaturated bonds, including alkenes and alkynes, and aryl cyanation strategies are described. While hydrogen cyanide is usually implemented on industrial scales, HCN-free transfer …
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Challenging the Limitations of the Streitwieser Lithium Indicator Acidity Scale with Cyclopentadiene Derivatives
… our own synthetic method based on electrophilic cyanation of cyclopentadiene derivatives using tosyl cyanide (TsCN) as the cyanizing reagent. Neutral cyanocyclopentadienes are thermally unstable (likely they polymerize), so we developed workup procedures that maintained these compounds in their …
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NEW BIOCATALYTIC PLATFORMS FOR THE SYNTHESIS OF HIGHLY VALUABLE COMPOUNDS THROUGH INTENSIFIED BIOPROCESSES
… of an effective synthesis of nitriles avoiding cyanation agents or other toxic compounds by performing a simple dehydration of oximes in water. This process, possible thanks to aldoxime dehydratase enzymes (Oxds), has been optimised to overcome the limited stability of these groups of …
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Palladium-catalyzed reactions of ammonia, carbon monoxide, and cyanide
… A method for the palladium-catalyzed cyanation of aryl chlorides and aryl tosylates was developed. The catalyst formed from the combination of Pd[P(o-tol)3]2 and CyPF-t-Bu formed aryl nitriles via reaction with Zn(CN)2 in high yields with an unprecedented catalyst loadings of 0.8-1 mol …
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Stereoselective Heterocycle Synthesis via Alkene Difunctionalization: Bulky Phosphine Ligands Enable Pd-Catalyzed Arylhalogenation, Arylcyanation and Diarylation
… a two highly diastereoselective Pd-catalyzed arylcyanation methodologies which were inspired by a challanging alkylation step in the aforementioned formal synthesis. The first methodology generates enantioenriched nitrile-containing dihydroisoquinolinones, and was found to irradicate multiple …
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Novel Organometallic Mixed Valence Complexes
… rather than cyano containing complexes. The cyanation reagent of choice is 1-cyano-4-dimethylaminopyridinium tetrafluoroborate ([CAP]BF4) which allows the ready synthesis of mono- and di-cyanovinylidenes, as well as the synthesis of cyanoacetylide containing complexes. The cyanating agent …