Ferrocenium Boronic Acid Catalyzed Deoxygenative Coupling of Alcohols with Carbon- and Nitrogen-Based Borate and Silane Nucleophiles
Bibliographic record
Abstract
High Resolution Image Download MS PowerPoint Slide A boronic acid catalyzed carbon–carbon and carbon–nitrogen bond-forming reaction for the functionalization of various π-activated alcohols has been developed. Ferrocenium boronic acid hexafluoroantimonate salt was identified as an effective catalyst in the direct deoxygenative coupling of alcohols with a variety of potassium trifluoroborate and organosilane nucleophiles. In a comparison between these two classes of nucleophiles, the use of organosilanes leads to higher reaction yields, increased diversity of the alcohol substrate scope, and high E / Z selectivity. Furthermore, the reaction proceeds under mild conditions and yields up to 98%. Computational studies provide a rationalization for a mechanistic pathway for the retention of E / Z stereochemistry when E or Z alkenyl silanes are used as nucleophiles. This methodology is complementary to existing methodologies for deoxygenative coupling reactions involving organosilanes, and it is effective with a variety of organosilane nucleophile sub-types, including allylic, vinylic, and propargylic trimethylsilanes.
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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".