En Route to Direct Cross-Coupling between Carbonyl Derivatives and Allyl Alcohols via Hydrazones
Bibliographic record
Abstract
Allylic cross-couplings are pivotal in the organic chemistry toolbox; however, traditional methods require the extensive use of noble metals and are limited to activated substrates. To date, allylic cross-couplings that utilize affordable metals and unactivated allylic alcohols remain unexplored. Herein, we report a distinct coupling of ubiquitous and commercially available aldehydes with unactivated allyl alcohols, which also benefits from generating only water and nitrogen gas as innocuous byproducts. This operationally simple and mild methodology enables the direct allylation of carbonyl derivatives, affording alkene products in moderate to high yields across 40 substrates. The reported conditions tolerate both aryl and alkyl aldehydes, as well as ketones with a variety of functional groups. Notably, our strategy facilitates the expedited synthesis of value-added chemicals while producing environmentally benign byproducts.
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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 | 0.001 |
| 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 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".