Synthesis and Characterization of Biguanide and Biguanidium Surfactants for Efficient and Recyclable Application in the Suzuki–Miyaura Reaction
Bibliographic record
Abstract
High Resolution Image Download MS PowerPoint Slide We report here the synthesis and thorough characterization of a new family of alkylbiguanides and alkylbiguanidium chlorides by 1 H and 13 C NMR and X-ray diffraction. Their critical micelle concentration was first determined by surface tension measurements. Hexylbiguanide was then studied as a surfactant in the micellar Suzuki–Miyaura cross-coupling reaction. The unexpected low reactivity of the system at high Pd/hexylbiguanide ratios was due to the change of the size and the shape of the aggregates, observed by transmission electron microscopy. The best catalytic activity was obtained for a 1:1 Pd/hexylbiguanide ratio for which the micellar conditions were conserved. Better results were obtained for several substrates, when compared to those previously obtained with metformin under the same reaction conditions. Higher yields and a better recyclability were obtained under micellar conditions with hexylbiguanide.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| 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 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
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 teacher head, 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".