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 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 | 0.004 | 0.003 |
| Meta-epidemiology (narrow) | 0.005 | 0.005 |
| Meta-epidemiology (broad) | 0.004 | 0.003 |
| Bibliometrics | 0.002 | 0.005 |
| Science and technology studies | 0.004 | 0.003 |
| Scholarly communication | 0.003 | 0.005 |
| Open science | 0.003 | 0.001 |
| Research integrity | 0.003 | 0.005 |
| Insufficient payload (model declined to judge) | 0.000 | 0.002 |
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; both teacher heads agree on what is shown here.
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".