Origin of Protonation Side Products in Pd-Catalyzed Decarboxylative Allylation Reactions: Evidence for In Situ Modification of Triphenylphosphine Ligand
Bibliographic record
Abstract
Palladium-catalyzed decarboxylative allylation (DcA) is a well-established method of carbon-carbon bond formation. This type of coupling is quite attractive, as the only byproduct is CO2. While a wide variety of ligands have been employed with Pd(0) or Pd(II) precatalysts in DcA reactions, the ligand structure is most often based on a triarylphosphine core. Despite their demonstrated utility, DcA processes have been hindered by the formation of protonation side products. While this phenomenon has been widely acknowledged, little has been reported on the origin of the proton. Herein, we address this and provide multiple lines of experimental evidence for the proton originating from the triarylphosphine ligand.
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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 | 0.001 | 0.009 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 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".