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Record W4415818289 · doi:10.1021/acs.orglett.5c03934

Ruthenium-Catalyzed C(sp <sup>2</sup> )–H Activation Using Pyridine and Imidazopyridine as Directing Groups for Selective Silylation

2025· article· en· W4415818289 on OpenAlexaff
Shengzhou Jin, Yu Wang, Ting Xu, Sai Zhang, Yao Zhou, Guigen Li

Bibliographic record

VenueOrganic Letters · 2025
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsInstitute of Aging
FundersNational Natural Science Foundation of ChinaWelch Foundation
KeywordsImidazopyridineSilylationDerivatizationRegioselectivityPyridineCatalysisHydrosilylationReaction conditions

Abstract

fetched live from OpenAlex

Ruthenium-catalyzed C(sp 2 )–H activation using pyridine and imidazopyridine directing groups enables direct ortho-silylation of 2-arylimidazoheterocycles with hydrosilanes as silylation reagents. This method achieves regioselective C(sp 2 )–H silylation without the need for preactivation, affording ortho-silylated arylimidazo[1,2- a ]pyridines in high yields. Notably, this represents the first example of hydrosilane coupling with imidazo[1,2- a ]pyridines via pentacyclometalated intermediates. The scalable protocol is compatible with a broad range of 2-aryl nitrogen-containing heterocycles. Experimental studies support the proposed catalytic cycle, and downstream derivatization reactions highlight the synthetic utility of the products. Furthermore, long-term cycling tests of NCM811||Li cells demonstrate that the silylated product, used as an electrolyte additive, significantly improves the cathode-electrolyte interfacial stability.

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 distilled prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
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 score0.096
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

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

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.

Opus teacher head0.016
GPT teacher head0.272
Teacher spread0.256 · 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 teacher head, not a consensus.

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

Citations1
Published2025
Admission routes1
Has abstractyes

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