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Record W4384498649 · doi:10.1002/cctc.202300649

Bifunctional Activation of NHC‐Zinc Pre‐Catalyst for Effective Hydroboration of Quinolines and Nitriles

2023· article· en· W4384498649 on OpenAlexafffund
Saeed Ataie, R. Tom Baker

Bibliographic record

VenueChemCatChem · 2023
Typearticle
Languageen
FieldChemistry
TopicOrganoboron and organosilicon chemistry
Canadian institutionsUniversity of Ottawa
FundersNatural Sciences and Engineering Research Council of CanadaCanada Research Chairs
KeywordsHydroborationChemistryBifunctionalQuinolineCatalysisZincStoichiometryMedicinal chemistryBifunctional catalystNitrileCatalytic cycleLigand (biochemistry)Organic chemistry

Abstract

fetched live from OpenAlex

Abstract Zinc dihydride complexes supported by bulky N‐heterocyclic carbenes (NHC) are efficient catalysts in hydroboration reactions. Herein, a set of zinc complexes with an amino‐pyrrolide chelate (H L 1 ) and the small NHC ligand, 2,3‐dimethyl‐3,4‐dichloroimidazol‐2‐ylidene (DDI) was synthesized and characterized. In particular, Zn(H L 1 ) 2 (DDI) ( Zn4) displayed high activity in catalytic nitrile dihydroboration using 0.01 mol % loading, and quinoline hydroboration using 0.05 mol % loading at room temperature. Stoichiometric reaction of Zn4 with 4 equiv. of pinacolborane (HBpin) produced ZnH 2 (DDI) ( Zn5 ) and 2 equiv. of dissociated (Bpin) 2 L 1 . Complex Zn5 , generated in situ by this bifunctional catalyst activation step, was shown to be more active than the bis‐NHC analog ZnH 2 (DDI) 2 and previously reported examples with bulky NHC ligands. In addition, variable time normalization analysis (VTNA) showed first‐order dependence on [quinoline], [HBpin] and [ Zn4 ], revealing that a single Zn−H is involved in the catalytic cycle, as was also observed in the stoichiometric reaction of Zn5 with quinoline. VTNA also indicated that this catalyst faces neither deactivation nor product inhibition.

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)0.000
Version: codex-gemma-dda1882f352aValidation 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 score0.004
Threshold uncertainty score0.653

Codex and Gemma teacher scores by category

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 integrity0.0000.000
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 head0.011
GPT teacher head0.249
Teacher spread0.238 · 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.

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

Citations13
Published2023
Admission routes2
Has abstractyes

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