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Record W2092537765 · doi:10.1021/om030003v

Synthesis, Structure, and Reactivity of an Unusual Platinum Olefin Carbene Complex, [(η<sup>4</sup>-cod)Pt{C(Ph<sub>2</sub>PNSiMe<sub>3</sub>)<sub>2</sub>-κ<i>C</i>,κ<i>N</i>}]

2003· article· en· W2092537765 on OpenAlexaff
Nathan D. Jones, Guanyang Lin, Robert A. Gossage, Robert McDonald, Ronald G. Cavell

Bibliographic record

VenueOrganometallics · 2003
Typearticle
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsUniversity of Alberta
Fundersnot available
KeywordsChemistryCarbeneDenticityMedicinal chemistryPhosphinePyridineElectrophileNucleophileLigand (biochemistry)PlatinumMetalationStereochemistryMetalOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

The organolithium dimer [Li 2 C(Ph 2 P NSiMe 3 ) 2 ] 2 ([Li 2 - 1 ] 2 ) reacts with 2 equiv of [PtCl 2 (cod)] (cod = 1,5-cyclooctadiene) in Et 2 O solution to give the novel Pt−carbene complex [(η 4 -cod)Pt{ C(Ph 2 P NSiMe 3 ) 2 -κ C,κ N }] ( 2 ), which is characterized by a relatively long Pt−C(carbene) bond and relatively short Pt−C(olefin) interactions indicative of an electron-rich Pt center. Under oxygen- and moisture-free conditions, 2 is remarkably inert; the cod ligand is not displaced by either monodentate or bidentate phosphines, phosphine sulfide, phosphite, or pyridine at room temperature, nor is the four-membered C,N-chelate ring opened by these reagents. However, 2 reacts with the electrophiles MeOTf (OTf = trifluoromethanesulfonate) and CO 2 . In the former case, the uncoordinated N atom of 2 is methylated to form [(η 4 -cod)Pt{ C(Ph 2 P NSiMe 3 )(Ph 2 P N(Me)SiMe 3 -κ C,κ N }][OTf] ( 3 ). In the latter, initial nucleophilic attack by the uncoordinated N atom on CO 2, followed by trimethylsilyl group migration from N to O, gives [(η 4 -cod)Pt{ C(Ph 2 P NSiMe 3 )(Ph 2 P NC(O)OSiMe 3 -κ C,κ N }] ( 4 ). Heating a benzene solution of 2 to 100 °C in a sealed tube for several hours, or to 60 °C for 10 min in the presence of H 2 O, yields the ortho-metalated complex [(η 4 -cod)Pt{CH(Ph(C 6 H 4 )P NSiMe 3 )(Ph 2 P NSiMe 3 )-κ C,κ C ‘ }] ( 5 ), which is characterized by Pt−C distances that are in the typical range for Pt−C(alkyl) and Pt−C(arene) interactions. The diastereoselectivity of the ortho metalation is consistent with an oxidative addition (nucleophilic) reaction mechanism for the ortho metalation. In contrast to 2, 5 displays typical cod substitution reactivity with chelating phosphines. The reaction between [Li 2 - 1 ] 2 and [PtCl 2 (cod)] in C 6 H 6 solution proceeds only very slowly and gives [Li][Pt{CH(Ph(C 6 H 4 )P NSiMe 3 )(Ph 2 P NSiMe 3 )-κ C,κ C ‘ }{CH(Ph 2 P NSiMe 3 ) 2 -κ C,κ N }] ( 7 ) in low yield.

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)0.0010.000

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 head0.014
GPT teacher head0.231
Teacher spread0.218 · 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

Citations89
Published2003
Admission routes1
Has abstractyes

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