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Record W2570591355 · doi:10.1002/chem.201605490

Pd‐PEPPSI‐IPent<sup>Cl</sup>: A Useful Catalyst for the Coupling of 2‐Aminopyridine Derivatives

2017· article· en· W2570591355 on OpenAlexafffund
Abir Khadra, Stanislas Mayer, Michael G. Organ

Bibliographic record

VenueChemistry - A European Journal · 2017
Typearticle
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsUniversity of OttawaYork University
FundersNatural Sciences and Engineering Research Council of CanadaEli Lilly and Company
KeywordsArylChemistryCatalysis2-AminopyridinePyridineReactivity (psychology)Potassium carbonateBase (topology)Medicinal chemistryOrganic chemistryCombinatorial chemistryPolymer chemistryAlkyl

Abstract

fetched live from OpenAlex

precatalyst (PEPPSI=pyridine-enhanced precatalyst preparation stabilisation initiation) has been demonstrated to be highly effective in the coupling of hetero(aryl)chlorides to free 2-aminopyridine substrates to produce N-(hetero)aryl-2-aminopyridine derivatives. The catalyst has proven to be competent in a number of other difficult cross-coupling reactions owing to the combination of the 3-pentyl-substituted N-aryl groups and the chlorines on the backbone of the N-heterocyclic carbene (NHC) core. This same reactivity here allows couplings to take place under very mild conditions (e.g., NaBHT (BHT=2,6-di-tert-butyl-4-methylphenol) or carbonate base) such that sensitive functional groups including esters, ketones and nitriles are tolerated. Key is that the same bulk that drives the cross-coupling also mitigates poisoning of the Pd centre with the 2-aminopyridine functionality in the starting materials and/or products, which forces the catalyst into inactive, stable resting states.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.001
Threshold uncertainty score0.003

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0010.001

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.

Opus teacher head0.037
GPT teacher head0.284
Teacher spread0.247 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

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".

Quick stats

Citations46
Published2017
Admission routes2
Has abstractyes

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