[(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 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 | 0.000 |
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 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".