Direct Boronic Acid Promoted Amidation of Carboxylic Acids with Poorly Nucleophilic Amines
Bibliographic record
Abstract
Abstract Direct amidation of carboxylic acids with poorly nucleophilic amines such as anilines is a notorious challenge in organic chemistry. Previously reported methodologies for direct amidation tend to report none or just a few examples with simple anilines, which generally react at temperatures over 100 °C. To address this challenge and develop a mild and direct dehydrative anilide synthesis, herein a series of novel boronic acids with a biphenyl scaffold were prepared based on a design concept of bifunctional activation. The optimal thioether‐substituted biphenylboronic acid, 1e , exhibits good reactivity in promoting the amidation reaction of various anilines at 85 °C in fluorobenzene, including halogenated anilines, electron‐rich and electron‐deficient anilines, and the heterocyclic 6‐aminoquinoline. Variations of the aliphatic carboxylic acid are possible, affording the corresponding anilides in good yields. The efficiency and recyclability of boronic acid 1e were demonstrated on a gram‐scale amidation reaction.
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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 | 0.000 |
| 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) | 0.001 | 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".