Palladium-Catalyzed Carbonylation of Aryl Chlorides to Electrophilic Aroyl-DMAP Salts
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Bibliographic record
Abstract
The palladium-catalyzed carbonylative coupling of aryl chlorides and 4-dimethylaminopyridine (DMAP) to generate electrophilic aroyl-DMAP salts is described. In contrast to classical carbonylation reactions, which often require nucleophiles to react with weakly electrophilic palladium-acyl intermediates, the high electrophilicity of aroyl-DMAP salts allows the acylation of a broad range of substrates. This transformation is mediated by a palladium-Xantphos catalyst, and mechanistic studies suggest the combination of ligand steric strain together with Pd(0) stabilization allows both the reductive elimination of a reactive ArCO–DMAP product and oxidative addition of the strong aryl-chloride bond. Overall, this transformation allows the generation of amides and esters from aryl chlorides with an array of nucleophiles and with good functional group compatibility.
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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 | 0.001 |
| 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) | 0.000 | 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