Pd(η<sup>3</sup>-1-PhC<sub>3</sub>H<sub>4</sub>)(η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>), an Unusually Effective Catalyst Precursor for Heck–Mizoroki and Sonogashira Cross-Coupling Reactions Catalyzed by Bis-Phosphine Palladium(0) Compounds
Bibliographic record
Abstract
The compound Pd(η 3 -1-PhC 3 H 4 )(η 5 -C 5 H 5 ) reacts essentially quantitatively with a variety of phosphines L to form cross-coupling catalysts of the type PdL 2 and has recently been shown to be a much more effective catalyst precursor for Suzuki–Miyaura cross-coupling reactions in comparison to more commonly utilized precursors such as Pd(PPh 3 ) 4, Pd 2 (dba) 3, and Pd(OAc) 2, which do not effectively generate two-coordinate species PdL 2 . This advantage is expected to apply also to e.g. Heck-Mizoroki and Sonogashira cross-coupling reactions, both of which are generally believed to be catalyzed by species of the type PdL 2 . Therefore, comparisons of the efficacies of catalyst systems based on Pd(η 3 -1-PhC 3 H 4 )(η 5 -C 5 H 5 ), Pd(PPh 3 ) 4, Pd 2 (dba) 3, and Pd(OAc) 2 are made utilizing the conventional coupling reactions of aryl halides with methyl acrylate and styrene for Heck–Mizoroki coupling and with phenylacetylene for Sonogashira coupling. As anticipated, catalyst systems based on Pd(η 3 -1-PhC 3 H 4 )(η 5 -C 5 H 5 ) are found to be significantly more active.
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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) | 0.000 | 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 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 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".