Site-Selective Benzylic C–H Hydroxylation in Electron-Deficient Azaheterocycles
Bibliographic record
Abstract
Benzylic C–H bonds can be converted into numerous functional groups, often by mechanisms that involve hydrogen atom transfer at the key bond breaking step. The abstracting species is most often an electrophilic radical, which makes these reactions best suited to electron-rich C–H bonds to achieve appropriate polarity matching. Thus, electron deficient systems such as pyridine and pyrimidine are relatively unreactive, and relatively underrpresented in substrate scopes. In this report, we describe a new method for benzylic hydroxylation—essentially an unknown reaction in the case of pyrimidines—that makes use of an iodine(III) reagent to affords very high selectivity towards electron-deficient azaheterocycles in substrates with more than one reactive position and prevents over-oxidation to carbonyl products. The identification of key reaction byproducts supports a mechanism that involves radical coupling in the bond forming step.
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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 | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.001 |
| 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 | 0.001 |
| Research integrity | 0.001 | 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".