Simple copper/TEMPO catalyzed aerobic dehydrogenation of benzylic amines and anilines
Why this work is in the frame
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Bibliographic record
Abstract
CuBr(2) with 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) has been successfully employed for the aerobic oxidation of primary and secondary benzyl amines in aqueous acetonitrile. Such catalytic systems have previously been used extensively in alcohol oxidation reactions. The same catalyst system was also used for oxidative cross-couplings of benzylamines with anilines. The electronic and steric properties of the aniline partner were found to be of crucial importance in determining reactivity or lack thereof. A mechanism for these reactions is proposed based on the data obtained to date. In the absence of benzyl amines, electron-rich anilines were found to undergo dehydrogenative coupling and yields of the resulting azo products could be increased by replacing CuBr(2) with CuBr. No ligand (e.g. pyridine) is required for either reaction to proceed and presumably water and acetonitrile solvate the copper-containing intermediates.
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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 | 0.000 | 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) | 0.004 | 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