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Record W4395039924 · doi:10.1002/adsc.202301409

Tetrafluoroethylation of Electron‐Rich Alkenyl Iodides Enabled by <i>in situ</i> Generation of Solvent‐Stabilized “Ligandless” CuCF<sub>2</sub>CF<sub>2</sub>H

2024· article· en· W4395039924 on OpenAlex
Cristina Maria Segovia, Luana L. T. N. Porto, Paula Casasús, Isabel Bascuas, Amena Ahmad, Jordi Mestre, Miguel Bernús Pérez, Sergio Castillón, R. Tom Baker, Omar Boutureira

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.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueAdvanced Synthesis & Catalysis · 2024
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicFluorine in Organic Chemistry
Canadian institutionsUniversity of Ottawa
FundersEuropean Regional Development FundNatural Sciences and Engineering Research Council of CanadaAgencia Estatal de InvestigaciónMinisterio de Ciencia, Innovación y UniversidadesCanada Research ChairsUniversitat Rovira i VirgiliFlorida Polytechnic University
KeywordsChemistrySolventIn situOrganic chemistry

Abstract

fetched live from OpenAlex

Abstract In this study, we have developed a metal‐mediated synthetic method for incorporating the 1,1,2,2‐tetrafluoroethyl (CF 2 CF 2 H) motif into unactivated, electron‐rich alkenyl iodides using cross‐coupling reactions. We discovered that the stable Cu(CF 2 CF 2 H)(PPh 2 Me) 3 complex, while unreactive with these substrates, serves as a P‐ligated reservoir for the formation of solvent‐stabilized “ligandless” and reactive CuCF 2 CF 2 H species. This transformation occurs upon addition of CuBr, which partially scavenges the P‐ligand in the form of CuBr(PPh 2 Me) 3 . The resulting in situ generated solvent stabilized “ligandless” system significantly enhances the reactivity of the complex, particularly towards challenging electron‐rich substrates. This advancement enables the synthesis of HCF 2 CF 2 ‐glycals, as well as nucleosides/nucleobases and arenes.

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)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
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 score0.033
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0010.001
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 head0.029
GPT teacher head0.332
Teacher spread0.303 · 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