Pd‐PEPPSI Complexes and the Negishi Reaction
Why this work is in the frame
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Bibliographic record
Abstract
Abstract An overview of Pd‐PEPPSI complexes in the Negishi cross‐coupling reaction is presented. Preliminary evaluations of differentially substituted imidazolium salts that generate highly active cross‐coupling catalysts in situ provide the foundation for the development of an air‐ and moisture‐stable NHC‐based precatalyst: Pd‐PEPPSI‐IPr. The application of Pd‐PEPPSI‐IPr in sp 3 –sp 3 , sp 3 –sp 2 (and vice versa), and sp 2 –sp 2 Negishi cross‐couplings is reviewed. This allowed the systematic development of Pd‐PEPPSI‐IPent, a more sterically demanding, second‐generation catalyst that outperforms the IPr analogue in a variety of sp 2 –sp 2 Negishi cross‐couplings. General routes for the preparation of organozinc reagents are also examined, and an additives study reveals the probable transmetallating species that is operative in these cross‐couplings. Mechanistic considerations of the Negishi cross‐coupling reaction based on experimental and computational studies are summarized and evaluated.
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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 | 0.001 | 0.001 |
| 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 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 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