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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 OpenAlex
Nathan D. Jones, Guanyang Lin, Robert A. Gossage, Robert McDonald, Ronald G. Cavell

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 · 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.

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)0.001
metaresearch head score (Gemma)0.002
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
Consensus categoriesMeta-epidemiology (narrow)
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 score0.006
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.002
Meta-epidemiology (narrow)0.0020.002
Meta-epidemiology (broad)0.0020.001
Bibliometrics0.0010.002
Science and technology studies0.0010.001
Scholarly communication0.0000.001
Open science0.0010.000
Research integrity0.0010.002
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 head0.014
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