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Record W2008710702 · doi:10.1021/om700400x

New Pincer-Type Diphosphinito (POCOP) Complexes of Nickel

2007· article· en· W2008710702 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueOrganometallics · 2007
Typearticle
Languageen
FieldChemistry
TopicOrganometallic Complex Synthesis and Catalysis
Canadian institutionsUniversité de Montréal
Fundersnot available
KeywordsChemistryPincer movementYield (engineering)Medicinal chemistryLigand (biochemistry)AcetonitrileAlkylationMetalationNickelCationic polymerizationPincer ligandAlkylAdductAcrylonitrileToluenePolymer chemistryCatalysisOrganic chemistry

Abstract

fetched live from OpenAlex

This report describes the synthesis, characterization, and reactivities of a new series of pincer-type nickel complexes based on the diphosphinito (POCOP) ligands 1,3-( i- Pr 2 PO) 2 C 6 H 4, 1, and ( i -Pr 2 POCH 2 ) 2 CH 2, 2 . Reacting these ligands with (THF) 1.5 NiCl 2, (THF) 2 NiBr 2, or (CH 3 CN) n NiX 2 (X = Br, n = 2; I, n = 3) gives pincer-type complexes by metalation of the central carbon atom. The yields of these (POCOP)NiX complexes vary with the type of ligand and Ni precursor used, as well as the reaction conditions. In general, the aromatic ligand 1 was metalated more readily to give excellent yields of the pincer complexes {2,6-( i- Pr 2 PO) 2 C 6 H 3 }NiX (X = Cl, 1a, 85% yield; X = Br, 1b, 95% yield; X = I, 1c, 85% yield), especially when the reaction mixture was heated to 60 °C for 1 h in the presence of 1 equiv of 4-dimethylaminopyridine (DMAP). The analogous reactions of ligand 2 were more sluggish and required refluxing in toluene to give {( i -Pr 2 POCH 2 ) 2 CH}NiX (X = Cl, 2a, 33% yield; X = Br, 2b, 93% yield; X = I, 2c, 70% yield). Displacement of Br from 1b and 2b by Ag(O 3 SCF 3 ), acetonitrile, or acrylonitrile gave, respectively, the neutral Ni−O 3 SCF 3 derivatives 1d and 2d and the cationic adducts of CH 3 CN ( 1e and 2e ) and CH 2 CHCN ( 1f and 2f ). Reacting 1b with MeMgCl or EtMgCl gave the corresponding Ni−alkyl derivatives 1g and 1h, respectively, whereas alkylation of complexes 2a − c was unsuccessful. The POC sp3 OP-based complexes 2a and 2b could be oxidized to paramagnetic, 17-electron species {( i -Pr 2 POCH 2 ) 2 CH}Ni III X 2 (X = Cl, 2i; Br, 2j ). Solid-state structures are reported for Ni−halide derivatives, the neutral complexes 2d, 1g, and 1h, the cationic adduct 1e, and the Ni(III) derivative 2i . The cationic acrylonitrile derivative 1f promotes the Michael addition of morpholine, cyclohexyl amine, or aniline to acrylonitrile, methacrylonitrile, or crotonitrile, whereas the paramagnetic Ni III complex 2j promotes the addition of CCl 4 to methyl acrylate, methyl methacrylate, styrene, 4-methylstyrene, acrolein, and acrylonitrile (Kharasch reaction).

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.

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 categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
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 score0.262
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0940.000

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 head0.017
GPT teacher head0.248
Teacher spread0.231 · 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