MétaCan
Menu
Back to cohort
Record W2325331844 · doi:10.1021/om400883u

(<i>N</i>-Phosphinoamidinate)Iron Pre-Catalysts for the Room Temperature Hydrosilylation of Carbonyl Compounds with Broad Substrate Scope at Low Loadings

2013· article· en· W2325331844 on OpenAlexaff
Adam J. Ruddy, Colin M. Kelly, Sarah M. Crawford, Craig A. Wheaton, Orson L. Sydora, Brooke L. Small, Mark Stradiotto, Laura Turculet

Bibliographic record

VenueOrganometallics · 2013
Typearticle
Languageen
FieldChemistry
TopicAsymmetric Hydrogenation and Catalysis
Canadian institutionsDalhousie University
Fundersnot available
KeywordsHydrosilylationPhenylsilaneChemistryAcetophenoneCatalysisSubstrate (aquarium)SolventYield (engineering)Organic chemistryLigand (biochemistry)CobaltPolymer chemistryMedicinal chemistry

Abstract

fetched live from OpenAlex

The synthesis and structural characterization of three-coordinate iron(II) and cobalt(II) complexes supported by new N -phosphinoamidinate ligands is reported, along with the successful application of these complexes as precatalysts for the challenging room-temperature hydrosilylation of carbonyl compounds to afford alcohols upon workup. Under the rigorous screening conditions employed (0.015 mol % Fe) for the reduction of acetophenone, the well-defined iron(II) amido precatalyst 2b, featuring bulky N -2,6-diisopropylphenyl and di- tert -butylphosphino moieties within the N -phosphinoamidinate ligand, exhibited exceptional catalytic performance. Further experimentation revealed that the yield achieved in the hydrosilylation of acetophenone employing 2b was unaltered when conducting reactions in the absence of light, in the presence of excess mercury, or under solvent-free conditions. Notably, precatalyst 2b was found to exhibit the broadest substrate scope reported to date for such room-temperature iron-catalyzed carbonyl hydrosilylations en route to alcohols, enabling the chemoselective reduction of structurally diverse aldehydes and ketones, as well as for the first time esters, at remarkably low loadings (0.01–1.0 mol % Fe) and using only 1 equiv of phenylsilane reductant.

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 score0.004

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 integrity0.0000.000
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 head0.006
GPT teacher head0.197
Teacher spread0.192 · 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

Citations113
Published2013
Admission routes1
Has abstractyes

Explore more

Same venueOrganometallicsSame topicAsymmetric Hydrogenation and CatalysisFrench-language works237,207