Homogeneously-Catalyzed Coupling Reactions in Switchable Solvents
Bibliographic record
Abstract
Due to the increasing environmental impact of society, it is imperative that current industrial processes be modified and new industrial processes be implemented in order to reduce environmental harm. However, these new or modified processes must be more energy-efficient, materials-efficient, and cost-effective so that they are more economically beneficial than the other processes. The described research was inspired by these two ideas and is comprised of two projects, both focused on the creation of recyclable, CO2-switchable methods of separating organic products, inorganic byproduct and catalyst. For the first part of the project, Suzuki-Miyaura cross-couplings were tested in switchable water, concentrating on the activation of aryl chlorides and product separation techniques. Switchable water, which is an aqueous solution of an amine, was used as solvent with the amine functioning as the base for the palladium-catalyzed Suzuki-Miyaura cross-coupling of activated aryl chlorides with phenyl boronic acid, using TPPTS (a water-soluble phosphine ligand). The use of Schlenk techniques resulted in conversion of 99% and isolated yields of 87% with the absence of homocoupling. For the second part of the project, the development of an easily prepared CO2-switchable polymeric ligand is described. The polymeric ligand was used in the Suzuki-Miyaura cross-coupling reaction for the synthesis of a biaryl product using 4-iodobenzaldehyde and phenylboronic acid pinacol ester in water. With the help of this switchable polymeric ligand, organic product, inorganic byproduct, and catalyst were separated into three fractions. A catalyst recycling system was developed for the Suzuki-Miyaura cross-coupling reaction. The catalyst was able to be recovered and reused, albeit with lower activity.
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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) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 0.001 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 0.002 |
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".