Modulating Electronic Properties of N‐Heterocyclic Carbene Ligands: Effects on the Pd‐Catalyzed Buchwald–Hartwig Amination
Bibliographic record
Abstract
N‐heterocyclic carbene (NHC) ligands featuring functional groups at remote positions allowing for electronic modifications were synthesized and their steric and electronic properties were investigated. The NHC ligands are found to possess comparable steric profiles while displaying similar, but varying electron donating capabilities. Palladium complexes coordinated to these ligands were synthesized, characterized, and investigated in the Buchwald–Hartwig Amination (BHA) of aryl chlorides under both strongly basic and weakly basic conditions. In both cases, we find that ligands possessing more electron donating substituents are more active in this transformation. We further report weakly basic conditions which gives the desired aminated product in high yield with low catalyst loading (0.5–2.0 mol%) that are more tolerant to base sensitive functional groups.
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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) | 0.000 | 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 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".