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Record W1970400201 · doi:10.1021/om049565k

Dihydridoamine and Hydridoamido Complexes of Ruthenium(II) with a Tetradentate P−N−N−P Donor Ligand

2004· article· en· W1970400201 on OpenAlexaff
Tianshu Li, Raphaël Churlaud, Alan J. Lough, Kamaluddin Abdur‐Rashid, Robert H. Morris

Bibliographic record

VenueOrganometallics · 2004
Typearticle
Languageen
FieldChemistry
TopicAsymmetric Hydrogenation and Catalysis
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsChemistryDeprotonationLigand (biochemistry)RutheniumMedicinal chemistryAcetophenoneCatalysisTolueneBenzeneStereochemistryOrganic chemistry

Abstract

fetched live from OpenAlex

The new diphosphinediimine ligand PPh 2 C 6 H 4 CH NCMe 2 CMe 2 N CHC 6 H 4 PPh 2 {tmeP 2 N 2 } is prepared by reacting NH 2 CMe 2 CMe 2 NH 2 with 2 equiv of PPh 2 (C 6 H 4 -2-CHO). The diamine derivative PPh 2 C 6 H 4 CH 2 NHCMe 2 CMe 2 NHCH 2 C 6 H 4 PPh 2 {tmeP 2 (NH) 2 } is prepared by reducing tmeP 2 N 2 with LiAlH 4 . The reaction of RuHCl(PPh 3 ) 3 with tmeP 2 N 2 in THF produces the complex trans -RuHCl{tmeP 2 N 2 }, while a similar reaction of RuHCl(PPh 3 ) 3 with tmeP 2 (NH) 2 gives the complex trans -RuHCl{tmeP 2 (NH) 2 }, as a mixture of two isomers. The isomer with two N−H bonds syn to the Ru−H bond is converted on heating to an isomer thought to have one N−H syn to the Ru−H. The reaction of the two isomers with KO t Bu under Ar in toluene produces the novel hydridoamido complex RuH{tmeP 2 NNH}, where the ligand is deprotonated at one nitrogen. Reaction of this amido complex with H 2 gives exclusively the dihydridoamine complex trans -Ru(H) 2 {tmeP 2 (NH) 2 }. The complexes have been characterized by X-ray crystallography, NMR, IR, elemental analysis, and a deuterium exchange study. Complex RuH{tmeP 2 NNH}, or a combination of RuHCl{tmeP 2 (NH) 2 } and KO t Bu, slowly catalyzes the hydrogenation of acetophenone (6 atm H 2, 20 °C, benzene or 2-propanol). The catalytic cycle is thought to be similar to that for the ketone hydrogenation precatalyst trans -RuHCl{(S,S)-cyP 2 (NH) 2 )}. However in the present work both of the proposed catalysts trans -RuH 2 {tmeP 2 (NH) 2 } and RuH{tmeP 2 NNH} have been completely characterized. The tmeP 2 (NH) 2 system, with hindering methyl groups, is less active than the cyP 2 (NH) 2 system with a trans -1,2-substituted cyclohexyl backbone. The variable configuration of the amine nitrogens that is observed for the tmeP 2 (NH) 2 complexes might also occur in the cyP 2 (NH) 2 systems and could explain the inconsistent selectivity of such catalysts. The diimine complex RuHCl{tmeP 2 N 2 } reacts with KO t Bu under H 2 to produce the dihydridodiamine complex trans -Ru(H) 2 {tmeP 2 (NH) 2 }, the catalyst for the hydrogenation of acetophenone.

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 score0.018
Threshold uncertainty score0.779

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.001
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 head0.008
GPT teacher head0.203
Teacher spread0.196 · 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

Citations85
Published2004
Admission routes1
Has abstractyes

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