MétaCan
Menu
Back to cohort
Record W1984625169 · doi:10.1021/om800247p

Insight into the Mechanism of Platinum-Catalyzed Cross-Coupling of Polyfluoroaryl Imines

2008· article· en· W1984625169 on OpenAlexaff
Tongen Wang, Jennifer A. Love

Bibliographic record

VenueOrganometallics · 2008
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicFluorine in Organic Chemistry
Canadian institutionsUniversity of British Columbia
Fundersnot available
KeywordsChemistryTransmetalationCatalysisImineBond cleavageReductive eliminationCleavage (geology)SubstituentMedicinal chemistryReaction mechanismCoupling reactionPlatinumStereochemistryPhotochemistryCombinatorial chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

We recently reported the first examples of Pt-catalyzed methylation of polyfluorinated arenes as a means to generate partially fluorinated aromatic building blocks. The reaction is selective for cleavage of C−F bonds ortho to an imine substituent and allows for preferential cleavage of C−F bonds in the presence of considerably weaker bonds (e.g., C−Br). We report herein the proposed mechanism for this reaction. Initial C−F activation generates a Pt(IV)−F intermediate, which then reacts with (CH 3 ) 2 Zn via transmetalation. Subsequent reductive elimination from the Pt(IV) species generates a new sp 2 −sp 3 C−C bond. In addition, we have identified a species present during the catalytic reaction and propose this to be the catalyst resting state.

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 score0.002
Threshold uncertainty score0.008

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 communication0.0000.001
Open science0.0010.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0020.001

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 head0.075
GPT teacher head0.376
Teacher spread0.300 · 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

Citations88
Published2008
Admission routes1
Has abstractyes

Explore more

Same venueOrganometallicsSame topicFluorine in Organic ChemistryFrench-language works237,207