Selective Zinc‐Catalyzed 1,2‐hydroboration of N‐heteroaromatics via a Non‐Hydride Mechanism
Bibliographic record
Abstract
Abstract A novel bidentate amine‐imine ligand precursor LH has been synthesized. This compound was reacted with ZnMe 2 to generate the zinc methyl complex, LZnMe ( 4 ). The latter compound was fully characterized by NMR spectroscopy and single crystal X‐ray diffraction. Compound 4 is a catalyst for the hydroboration and hydrosilylation of N‐heterocycles, but with moderate catalytic activity. A more active catalyst, the zinc hydride complex LZnH ( 5 ) was synthesized by reacting the lithium salt LLi with ZnCl 2 followed by sequential reaction with tBuOK and PhMeSiH 2 . Compound 5 catalyzes the selective 1,2‐hydroboration of nitrogen heteroaromatics with decreased catalyst load and under mild conditions. Deuterium‐labeling experiments and kinetic studies provided insight into the possible reaction mechanism. It is proposed that hydride transfer to the substrate proceeds directly from the reductant (borane) via a six‐membered transition state facilitated by the catalyst, in which it plays an ambiphilic role, activating the substrate via coordination to the Lewis acidic zinc and enhancing the hydricity of the borane through coordination to the zinc hydride.
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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 | 0.001 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| 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".