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Showing 1 to 17 of 17 for “"Csp3"”.
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Photoredox Generated Radicals In Csp2-Csp3 Bond Construction
The routine application of Csp3-hybridized nucleophiles in cross-coupling has been an ongoing pursuit in the agrochemical, pharmaceutical, and materials science industries for over 40 years. Unfortunately, despite numerous attempts to circumvent the problems associated with alkyl nucleophiles, …
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Stereospecific Csp3 cross-coupling for modular polyketide synthesis
… to this platform is an inability to generate Csp3-rich, stereochemically complex molecules due to challenges in the coupling of alkyl groups using Suzuki-Miyaura cross-coupling reactions. Here, I show that stereospecific palladium-catalyzed cross-coupling reactions of secondary alkyl …
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Palladium-Catalysed Functionalisation of Csp3–H Bonds Directed by Aliphatic Amines
… pharmaceutical agents. This thesis describes two Csp3–H functionalisation reactions, using native amines (secondary and tertiary) to direct C–H activation. Chapter 2 describes a palladium-catalysed Csp3–H acetoxylation directed by native secondary amines. A range of cyclic amines could be …
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Stereoselective synthesis and iterative coupling of Csp3 boronates for automating small molecule synthesis
… coupling of boronate building blocks to include Csp3-rich linear and polycyclic small molecules. The first approach undertaken was the discovery of a pinene-derived iminodiacetic acid (PIDA) ligand which enabled the stereoselective synthesis of a wide range of new types of Csp3 boronates. The …
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Ligand design principles for perfecting stereoretention in Suzuki-Miyaura cross-coupling of unactivated CSP3 boronic acids
… small molecules. Still, the lack of methods for Csp3 coupling dramatically limits the scope of building block-based synthesis. With the goal of developing a stereospecific cross-coupling reaction for unactivated secondary alkylboronic acids, it was critical to understand the competition between …
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Storing copper in Streptomyces lividans: structural and biochemical properties of a copper storage protein
… recently discovered cytosolic proteins known as Csp3. These members are exclusively found in the bacterial cytosol and comprise of a four-helix bundle that assemble into homotetramers and can bind between 70-80 Cu(I) ions through mainly Cys thiolate coordination. In Chapter 2 bioinformatic …
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Part I: synthesis and cross-coupling of the C1-C12 primary organoborane building block of amphotericin B; Part II: site- and stereoretentive cross-coupling of unactivated secondary boronic acids inspired by amphotericin B
… consecutive Csp2 centers on C1-C19 AmB skeleton, Csp3-Csp2 cross-coupling is required to assemble the polyol subunit BB1. The synthesis of BB1 turned out to be challenging. Moreover, a Csp3-Csp2 cross-coupling reaction was not readily available for the connection of BB1 and the rest of the …
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Expansion of the iterative cross-coupling synthesis strategy through Csp3 halide cross-coupling, Mida boronate synthesis, and chan-lam couplings
… cross-coupling platform. We report a mild Csp3 halide – Csp2boronic acid Suzuki-Miyaura cross-coupling method amenable to fine molecule synthesis. We also report a new method for the synthesis of MIDA boronates which are sensitive to current methods. Finally, we report the extension of the …
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Mechanistic investigations into the origin of chemoselectivity a methylene (csp3) c-h oxidation in the presence of α-β unsaturated carbonyls and exploration of reaction scope
Submission published under a 24 month embargo labeled 'Closed Access', the embargo will last until 2027-05-01
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Transition metal-catalyzed cross-coupling reactions of functionalized organometallic reagents
… of TBAI · the application of alkyl bromides in a Csp3-Csp3 cross-coupling reaction. Furthermore, · the presence of sensitive functional groups such as an amino function with an unprotected NH group is tolerated · coupling of diastereomerically enriched zinc reagents proceed with high retention of …
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Manganese-catalyzed C-H oxidation applied to the synthesis of complex molecules
… significant challenge in the field of undirected Csp3-H oxidation. The powerful oxidants required to functionalize these strong bonds often react with any oxidizable functional groups present in a substrate, furnishing undesired side products. Although there are many reports of applying C-H …
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STEREOSPECIFIC SUZUKI-MIYAURA CROSS-COUPLING OF CHIRAL BENZYLIC BORONIC ESTERS AND VINYL BROMIDES
… expanding the scope of our established Csp2-Csp3 coupling reaction with chiral boronic esters. By employing vinyl halides as electrophiles, we can stereospecifically prepare alkene-containing products—a useful handle for further functionalization.
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Síntesis de derivados orgánicos de bencil- y alilestaño y estudio de sus propiedades físicas y químicas
… correspondientes por formación de enlace Csp3(bencílico)-Csp2(arílico) con muy buen rendimiento y utilizando distintas condiciones de reacción. De acuerdo a los resultados obtenidos, hemos demostrado que la síntesis de estructuras aromáticas sustituídas que formen parte de compuestos de …
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Transition metal-catalyzed olefin functionalization for highly regio-, enantio-, and chemoselective C–X bond formation
… the newly formed C–N bond to afford a terminal Csp3–N bond and a ketone or styrene moiety. The functional group tolerance is explored and results of preliminary mechanistic investigations are shown.
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TRANSITION METAL CATALYZED CROSS-COUPLINGS OF ALKYL SULFONE ELECTROPHILES
… the early 1970’s, their potential as competent Csp3 electrophiles has not been recognized until recently. Our group has made significant contributions to the development of new cross-coupling methodologies utilizing alkyl sulfones as electrophiles. This thesis describes the use of alkyl sulfones …
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Towards the automation of small molecule synthesis: The development of an impact-prioritized list couplings and blocks for building block assembly of most linear natural products
… the stereoretentive cross-coupling of primary Csp3 boronic acids to vinyl halides, and rationally developed a new phosphine ligand that enables high yield and diastereospecificity for much of computationally pre-determined substrate scope. This coupling methodology can then be integrated into …
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FROM BATCH TO FLOW: RETHINK THE WAY OF DOING CHEMISTRY
… it is described a deoxygenative strategy for the Csp3-Csp2 cross-coupling reaction for the preparation of novel interesting tryptamine derivatives, by the use of photochemistry. First, we examine the use of metallaphotoredox chemistry to perform cross coupling reaction, then the importance of …