Palladium‐Catalyzed Synthesis of <i>N</i>‐Cyclohexyl Anilines from Phenols with Hydrazine or Hydroxylamine via N‐N/O Cleavage
Why this work is in the frame
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Bibliographic record
Abstract
Abstract Direct access to amines from biomass‐based phenols via deoxygenative transformation remains greatly challenging in organic synthesis. Herein, we present a palladium‐catalyzed deoxygenative amination of phenols (and their benzyl ether) with hydrazine as nitrogen source. The hydroxylamine/formic acid can be substituted for hydrazine in some cases. This deoxyamination features the involvement of a complex C−O bond and N−N/O bond‐cleavage process and allows for the construction of N ‐substituted cyclohexyl anilines from an array of phenols by finely controlling the reaction conditions in moderate to good yields. magnified image
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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 | 0.006 |
| Meta-epidemiology (narrow) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.002 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.001 | 0.001 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.002 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.004 | 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 it