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 Suzuki–Miyaura Cross-Coupling Reactions Catalyzed by Bis-Phosphine Palladium(0) Compounds
Bibliographic record
Abstract
It has previously been shown that the easily handled, heat- and air-stable compound Pd(η 3 -1-PhC 3 H 4 )(η 5 -C 5 H 5 ) ( Vb ) reacts rapidly with a wide variety of tertiary phosphines L to produce near-quantitative yields of the corresponding Pd(0) compounds PdL 2, which are widely believed to be the active species in many often-used cross-coupling catalyst systems based on Pd(PPh 3 ) 4 ( I ), Pd 2 (dba) 3 ( II ), PdCl 2 ( III ), and Pd(OAc) 2 ( IV ). However, catalyst precursors I – IV are in fact known to preferentially generate sterically hindered, three-coordinate Pd(0) species rather than two-coordinate PdL 2, and thus Vb is hypothetically expected to be a better catalyst precursor for e.g. Suzuki–Miyaura cross-coupling reactions. Utilizing the conventional Suzuki–Miyaura cross-coupling reaction of phenylboronic acid with bromoanisole, comparisons are made of the efficacies of catalyst systems based on Vb with those based on compounds I – IV (L = the representative phosphines PPh 3, PCy 3, PBu t 3 ). As anticipated, catalysts generated from Vb are significantly more competent and, as a bonus, Vb makes palladium(0) complexes PdL 2 available under rigorously anhydrous conditions.
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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) | 0.002 | 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".