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Record W4409405522 · doi:10.1002/ejoc.202500122

Ni‐Catalyzed Cross‐Electrophile Couplings of <i>N</i>‐Alkoxyphthalimides and Aryl Halides

2025· article· en· W4409405522 on OpenAlexafffund
John J. Monteith, Sophie A. L. Rousseaux

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2025
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsUniversity of Toronto
FundersNatural Sciences and Engineering Research Council of CanadaUniversity of TorontoCanada Foundation for InnovationAlfred P. Sloan Foundation
KeywordsChemistryElectrophileArylHalideCatalysisMedicinal chemistryOrganic chemistryAlkyl

Abstract

fetched live from OpenAlex

N‐alkoxyphthalimides represent a versatile class of redox‐active alcohol derivatives for carbon–carbon bond formation following activation by single‐electron reduction. Herein, key precedents using N‐alkoxyphthalimides for the formation of new carbon–carbon bonds under photochemical reaction conditions are first presented. The merger of these and other single‐electron activation strategies with Ni catalysis in various cross‐electrophile couplings with aryl halides is then highlighted. A particular focus is made on the mechanisms proposed for these Ni‐catalyzed reductive cross‐couplings. Concluding thoughts for future reaction design using N‐alkoxyphthalimides as redox‐active C(sp3)O derivatives in transition metal‐catalyzed cross‐couplings are also presented.

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 score0.007

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 science0.0010.000
Research integrity0.0000.001
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 head0.011
GPT teacher head0.258
Teacher spread0.247 · 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

Citations0
Published2025
Admission routes2
Has abstractyes

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