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Record W4416612918 · doi:10.1021/acs.orglett.5c04085

Photoinduced Cleavage of Alkenyl Fluorides for Nucleophilic Acyl Substitution via In Situ Generated Acyl Fluorides

2025· article· en· W4416612918 on OpenAlexfundno aff
Emma Gogarnoiu, Ajay H. Bansode, Joshua Paolillo, Joseph Bergen, Marvin Parasram

Bibliographic record

VenueOrganic Letters · 2025
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicFluorine in Organic Chemistry
Canadian institutionsnot available
FundersNational Institutes of HealthYork UniversityDeciphera PharmaceuticalsAmgenCamille and Henry Dreyfus FoundationNational Institute of General Medical SciencesAmgen Foundation
KeywordsNucleophilic acyl substitutionCleavage (geology)In situNucleophileNucleophilic substitutionReactivity (psychology)PhotoexcitationThioester

Abstract

fetched live from OpenAlex

Acyl fluorides are valuable intermediates due to their stability and unique reactivity with amines, enabling selective acyl substitution. We report a mild one-pot method to access amides, esters, and thioesters from alkenyl fluorides. Visible-light photoexcitation of 4-nitrophthalonitrile promotes cleavage of the alkenyl fluoride, forming acyl fluorides in situ for nucleophilic acyl substitution. This protocol offers broad utility as demonstrated in the synthesis of linear peptide fragments.

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 score0.006

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0020.000

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 head0.043
GPT teacher head0.358
Teacher spread0.315 · 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

Citations2
Published2025
Admission routes1
Has abstractyes

Explore more

Same venueOrganic LettersSame topicFluorine in Organic ChemistryFrench-language works237,207