Palladium-Catalyzed Cross-Coupling of Cyanohydrins with Aryl Bromides: Construction of Biaryl Ketones
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Bibliographic record
Abstract
Abstract The palladium-catalyzed cross-coupling of the lithium anion of aryl tert-butyldimethylsilyl-protected cyanohydrins with aryl bromides followed by in situ deprotection with fluoride ion provides a convenient and versatile approach to biaryl ketones. This protocol represents the first example of a palladium-catalyzed arylation of a cyanohydrin, which functions as an acyl anion equivalent. Hence, in contrast to classical cross-coupling reactions, the pronucleophile component is incorporated in the product to permit further functionalization. We then highlight the synthetic utility of the new method with applications to bioactive biaryl ketones and the construction of a triaryl diketone that has been used to prepare an extended tetrathiafulvalene.
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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 | 0.000 |
| 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) | 0.008 | 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