[(NHC)Pd(allyl)Cl] Precatalysts in The Hiyama Reaction of Aryl Chlorides with Aryl Trimethoxysilanes: A Study in Side Reactions
Bibliographic record
Abstract
Palladium N-heterocyclic carbene (NHC) complexes of the general type [(NHC)Pd(allyl)Cl] are investigated as precatalysts in the Hiyama reaction of aryl chlorides with phenyl trimethoxysilanes. High yields of biaryls products are obtained from aryl chlorides featuring electron withdrawing groups using precatalysts coordinated to NHC ligands with sterically smaller wingtip groups (IMes and SIMes). Unactivated aryl chlorides appeared to be poor substrates in this reaction. A mechanistic proposal which we believe explains this poor activity is outlined based on in situ analysis by 19 F NMR spectroscopy where PhSi(OMe) 3 reacts nonproductively with fluoride, halting the reaction prematurely, via at least two different pathways.
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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 | 0.001 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.001 | 0.003 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
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 teacher head, 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".