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Record W4362695979 · doi:10.1021/prechem.3c00035

Simple and Efficient Aromatic C–H Oxazolination

2023· article· en· W4362695979 on OpenAlexfundno aff
Qiu Shi, Yu Huang, Wenbo Liu

Bibliographic record

VenuePrecision Chemistry · 2023
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsnot available
FundersFundamental Research Funds for the Central UniversitiesNational Natural Science Foundation of ChinaSun Yat-sen UniversityGuangzhou Municipal Science and Technology BureauCentral University Basic Research Fund of ChinaMcGill University
KeywordsElectrophilic aromatic substitutionOxazolineChemistryElectrophileCarboxylic acidAromaticityCombinatorial chemistrySubstrate (aquarium)Organic chemistryStereochemistryMoleculeCatalysis

Abstract

fetched live from OpenAlex

Aromatic oxazolines are versatile in organic synthesis as directing groups, ligands, and protected carboxylic acids. Developing efficient approaches to oxazoline from an aromatic C-H bond is more desirable compared to the established protocols from carboxylic acid and its equivalents. Herein, a simple and efficient aromatic C-H oxazolination with broad substrate scope is described. By employing this transformation as an enabling step, diversity-oriented synthesis of functionalized arenes and target-oriented synthesis of four drugs were accomplished. Mechanistic experiments suggest that this aromatic oxazolination is an electrophilic aromatic substitution. It is anticipated that this transformation will find applications in aromatic C-H functionalization with oxazoline either as a removable directing group or as a masked carboxylic acid.

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 science0.0000.000
Research integrity0.0000.001
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 head0.025
GPT teacher head0.313
Teacher spread0.288 · 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

Citations7
Published2023
Admission routes1
Has abstractyes

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