C2, C5, and C4 Azole <i>N</i>-Oxide Direct Arylation Including Room-Temperature Reactions
Why this work is in the frame
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Bibliographic record
Abstract
The N -oxide group imparts a dramatic increase in reactivity at all positions of the azole ring of thiazoles and imidazoles and changes the weak bias for C5 > C2 arylation to a reliable C2 > C5 > C4 reactivity profile. Use of this cross-coupling strategy enables high yielding and room-temperature C2 arylations, mild reactions at C5, and the first examples of C4 arylation providing a unique opportunity for exhaustive functionalization of the azole core with complete control of regioselectivity. A correlation of reactivity with the relative contributions of each carbon atom to the HOMO is observed and discussed.
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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 | 0.001 |
| 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 | 0.001 |
| Insufficient payload (model declined to judge) | 0.000 | 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