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>) as a Catalyst Precursor for Buchwald–Hartwig Amination Reactions
Bibliographic record
Abstract
The compound Pd(η 3 -1-Ph-C 3 H 4 )(η 5 -C 5 H 5 ) ( I ) reacts cleanly with many tertiary phosphines L to undergo reductive elimination of PhC 3 H 4 -C 5 H 5 and form palladium(0) species of the types PdL n ( n = 2, 3), long believed to be exemplary catalysts for Suzuki–Miyaura, Heck–Mizoroki, and Sonogashira cross-coupling reactions. I has accordingly been shown to be generally much more effective for these catalytic processes than are conventional catalyst precursors such as Pd(PPh 3 ) 4, Pd 2 (dba) 3, PdCl 2, and Pd(OAc) 2, in large part because I stands alone in this series for its ability to generate specifically and efficiently the desired species PdL 2 in many cases. We have now investigated I as a precursor for prototypical Buchwald–Hartwig amination reactions of 4-bromo- and 4-chloroanisole with morpholine, making comparisons with Pd 2 (dba) 3, Pd(OAc) 2, and [Pd(η 3 -1-Ph-C 3 H 4 )Cl] 2 ( IV ). In this work we have utilized PBu t 3 because of its general effectiveness, and we have also assessed XPhos and Mor-Dalphos, representatives of important classes of phosphines utilized elsewhere for amination reactions.
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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 | 0.003 | 0.006 |
| Meta-epidemiology (narrow) | 0.003 | 0.004 |
| Meta-epidemiology (broad) | 0.003 | 0.002 |
| Bibliometrics | 0.002 | 0.004 |
| Science and technology studies | 0.003 | 0.001 |
| Scholarly communication | 0.002 | 0.003 |
| Open science | 0.003 | 0.001 |
| Research integrity | 0.003 | 0.003 |
| Insufficient payload (model declined to judge) | 0.000 | 0.005 |
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".