Simple and Efficient Aromatic C–H Oxazolination
Why this work is in the frame
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Bibliographic record
Abstract
Aromatic oxazolines are versatile in organic synthesis as directing groups, ligands, and protected carboxylic acids. Developing efficient approaches to oxazoline from an aromatic C-H bond is more desirable compared to the established protocols from carboxylic acid and its equivalents. Herein, a simple and efficient aromatic C-H oxazolination with broad substrate scope is described. By employing this transformation as an enabling step, diversity-oriented synthesis of functionalized arenes and target-oriented synthesis of four drugs were accomplished. Mechanistic experiments suggest that this aromatic oxazolination is an electrophilic aromatic substitution. It is anticipated that this transformation will find applications in aromatic C-H functionalization with oxazoline either as a removable directing group or as a masked carboxylic acid.
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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 | 0.000 |
| Insufficient payload (model declined to judge) | 0.003 | 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