Chemo- and Regioselective Catalytic Reduction of N-Heterocycles by Silane
Bibliographic record
Abstract
The ruthenium complex [Cp( i Pr 3 P)Ru(NCCH 3 ) 2 ] + ( 1 ) catalyzes the regioselective hydrosilylation of pyridines to 1,4-dihydropyridines. Substitution in the 3- and 5-positions is tolerated, whereas pyridines with substituents in the 2-, 4-, and 6-positions are not reduced. Reduction of functionalized pyridines having keto and ester substituents results in a mixture of products. N -Silyl-1,4-dihydropyridine reacts with ketones and aldehydes to give products of N–Si addition across the C═O bond. Hydrosilylation of pyridine in acetone results quantitatively in the addition product PhMe 2 SiO–CMe 2 –NC 5 H 6, which decomposes in hexane to give the parent dihydropyridine HNC 5 H 6 . The phenanthroline complex [Cp(phen)Ru(NCCH 3 ) 2 ] + ( 10 ) catalyzes regioselective 1,4-reduction of phenanthroline by a 3–4-fold excess of silane/water or silane/alcohol mixtures. The Cp* analogue [Cp*(phen)Ru(NCCH 3 ) 2 ] + ( 9 ) catalyzes 1,4-regioselective monohydrosilylation of phenanthroline, quinoline, acridine, and 1,3,5-triazine and the 1,2-reduction of isoquinoline. In contrast, 2-substituted phenanthroline, pyrazine, 2-ethylpyridine, 2,6-lutidine, 2,4-lutidine, and pyrimidine are not reduced under these conditions by either of the catalysts studied.
Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.
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) | 0.001 | 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".