Part A: Palladium-Catalyzed CâH Bond Functionalization Part B: Studies Toward the Synthesis of Ginkgolide C using Gold(I) Catalysis
Bibliographic record
Abstract
The field of metal-catalyzed C–H bond functionalizations is an incredibly vibrant and spans beyond the formations of biaryl motifs. The introduction chapter will cover the mechanistic aspects of the C–H bond functionalization with metal-carboxylate complexes. The mechanistic facets of this reaction will be the main conducting line between the different sections and chapters of the first part of this thesis. In the second chapter, will be described additives that can readily promoted C–H bond arylation of poorly reactive substrates. More specifically, we will revisit the intramolecular direct arylation reaction we will demonstrate the effect of pivalic acid as a co-catalyst by developing milder reaction conditions. In the third chapter we be described experimental and computational studies which suggested that the a single pathway might be involved in the palladium-catalyzed C–H bond functionalization of a wide range of (hetero)arene. Following this we will describe a general set of conditions for the direct arylation of wide range of heteroarenes. Also, we will present two different strategies to selectively and predictably arylate substrates containing multiple functionalizable C–H bonds. In the fourth chapter will be presented our efforts toward the development of new C–H bond functionalization methods in which we could apply our knowledge on the C–H bond cleavage and apply it to the formation of new scaffolds. The development of two new palladium-catalyzed methods were also described. In the fifth chapter, our effort toward the development of ligands to specifically promoted C–H bond cleavage will be presented. In the sixth chapter will be presented the latest results on the study of the mechanism of the C–H bond cleavage combining experimental and computational studies. In part B of this thesis will be presented our strategy toward the total synthesis of ginkgolide C that included two gold(I)-catalyzed reactions as key steps in the preparation of the spiro[4.4]nonane core of this natural product. The first studies on the feasibility of the key steps of the synthesis will be described.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.005 | 0.001 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".