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Record W3033095630 · doi:10.1002/ejoc.202000672

Intramolecular Nickel‐Catalyzed Ring‐Opening Reactions of Oxabenzonorbornadienes with C<sub>1</sub>‐Tethered Aryl Halides: An Improvement of Method

2020· article· en· W3033095630 on OpenAlexafffund
Samuel Koh, Austin Pounder, Elizabeth Brown, William Tam

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2020
Typearticle
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsUniversity of Guelph
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryIntramolecular forceArylCatalysisHalideRing (chemistry)NickelPalladiumMedicinal chemistryTransition metalAryl halideCombinatorial chemistryPolymer chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

An improved method of the recently reported novel transition metal‐catalyzed intramolecular ring‐opening reaction of oxabenzonorbornadienes with C 1 ‐tethered aryl halides is described. Using a nickel catalyst, fused tetracycles containing a 1,2‐dihydronaphthalen‐1‐ol framework were generated with good to excellent yields and selectivities in most cases: a result seldom obtained using the previous palladium‐catalyzed conditions. Electron‐withdrawing, electron‐donating, and bulky substituents were generally found to be well tolerated in the reaction while extension of the tether led to decreased yields.

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 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 score0.002
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
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)0.0000.000

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 head0.013
GPT teacher head0.238
Teacher spread0.224 · 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 teacher head, not a consensus.

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

Citations11
Published2020
Admission routes2
Has abstractyes

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