Insight into the Mechanism of Platinum-Catalyzed Cross-Coupling of Polyfluoroaryl Imines
Bibliographic record
Abstract
We recently reported the first examples of Pt-catalyzed methylation of polyfluorinated arenes as a means to generate partially fluorinated aromatic building blocks. The reaction is selective for cleavage of C−F bonds ortho to an imine substituent and allows for preferential cleavage of C−F bonds in the presence of considerably weaker bonds (e.g., C−Br). We report herein the proposed mechanism for this reaction. Initial C−F activation generates a Pt(IV)−F intermediate, which then reacts with (CH 3 ) 2 Zn via transmetalation. Subsequent reductive elimination from the Pt(IV) species generates a new sp 2 −sp 3 C−C bond. In addition, we have identified a species present during the catalytic reaction and propose this to be the catalyst resting state.
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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 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.003 | 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".