Pd‐PEPPSI Complexes and the Negishi Reaction
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 sp3–sp3, sp3–sp2 (and vice versa), and sp2–sp2 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 sp2–sp2 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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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.001 | 0.001 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.003 | 0.001 |
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 source (direct Gemma or distilled Codex), 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".