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Record W1971588022 · doi:10.1002/ejoc.201000231

Copper‐Catalyzed Multicomponent Coupling of Organoindium Reagents with Nitrogen‐Containing Aromatic Heterocycles

2010· article· en· W1971588022 on OpenAlexaff
Ramsay E. Beveridge, D. A. Black, Bruce A. Arndtsen

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2010
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsMcGill University
Fundersnot available
KeywordsBenzothiazoleBenzoxazoleChemistryReagentPyridineCombinatorial chemistryCatalysisOrganic chemistryNitrogenCopperCoupling reactionPhthalazine

Abstract

fetched live from OpenAlex

Abstract A mild, copper‐catalyzed coupling of organoindium reagents with nitrogen‐containing aromatic heterocycles and chloroformates is described. This reaction proceeds with a range of organoindium reagents, yielding predominately or exclusively the 1,4‐addition products with pyridine. In addition, a range of other nitrogen‐containing heterocycles can be employed in this reaction (e.g. benzoxazole, benzothiazole, phthalazine). As an illustration of the utility of this reaction, this heterocycle functionalization is coupled with a subsequent oxidation to achieve the one‐pot synthesis of functionalized pyridine and benzothiazole derivatives.

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), Insufficient payload (model declined to judge)
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 score0.008
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
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)0.0030.000

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 head0.015
GPT teacher head0.238
Teacher spread0.223 · 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

Citations25
Published2010
Admission routes1
Has abstractyes

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