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Record W2071893350 · doi:10.1021/om020026u

Preparation of Dinuclear Phosphine-Bridged Palladium(II) Species and Their Silica-Bound Analogues as Catalysts for the Cyclization of Aminoalkynes

2002· article· en· W2071893350 on OpenAlexaff
Matthew K. Richmond, Susannah L. Scott, Glenn P. A. Yap, Howard Alper

Bibliographic record

VenueOrganometallics · 2002
Typearticle
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsUniversity of Ottawa
Fundersnot available
KeywordsChemistryPalladiumPhosphineCatalysisMedicinal chemistrySilanolReactivity (psychology)DichloromethaneProtonationMethylenePolymer chemistryMethylene bridgeStereochemistryOrganic chemistrySolvent

Abstract

fetched live from OpenAlex

Two new dinuclear palladium complexes, [Pd 2 Me 2 Cl 2 (dmpm) 2 ] ( 4 ) and [PdMe(Cl)(dmpm) 2 PdCl 2 ] ( 5 ), have been prepared and their structures determined by single-crystal X-ray analysis. 5 is an interesting example of a complex with both a cis -PdCl 2 center and a trans- MePdCl center, within the same molecule. The reactivity of 4, as well as the previously reported complexes [Pd 2 Me 2 Cl 2 (dppm) 2 ] ( 1 ), [Pd 2 ( μ -CH 2 )Cl 2 (dppm) 2 ] ( 2 ), and [Pd 2 Me 4 (dmpm) 2 ] ( 3 ), toward silica have been investigated. The complexes react readily with either dichloromethane or benzene suspensions of silica to give chemisorbed species, presumably by reaction of the Pd−Me group with the O−H bond of the surface silanol groups, in the case of 1, 3, and 4, and protonation of the methylene bridge, in the case of 2 . The complexes containing the more basic phosphine, dmpm, gave much higher palladium loadings (wt % Pd 1.37−2.47) on silica, compared to the dppm complexes (wt % Pd 0.55−0.80). The molecular and grafted materials were initially tested as catalysts for the cyclization of 6-aminohex-1-yne to give 2-methyl-1,2-dehydropiperidine. The silica/dmpm complexes were found to be the most active catalysts for this reaction and were also tested for the cyclization of 5-phenyl-4-pentyn-1-amine.

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 score0.009
Threshold uncertainty score0.542

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 head0.023
GPT teacher head0.262
Teacher spread0.239 · 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

Citations29
Published2002
Admission routes1
Has abstractyes

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