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Record W2754552369 · doi:10.1021/acs.orglett.7b02244

Palladium-Catalyzed Synthesis of 2-Cyanoindoles from 2-<i>gem</i>-Dihalovinylanilines

2017· article· en· W2754552369 on OpenAlexafffund
Nicolas Zeidan, Sabine Bognar, Sophia Lee, Mark Lautens

Bibliographic record

VenueOrganic Letters · 2017
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsUniversity of Toronto
FundersNatural Sciences and Engineering Research Council of CanadaUniversity of TorontoDeutscher Akademischer AustauschdienstAlphora Research
KeywordsChemistryCatalysisPalladiumSolventCombinatorial chemistrySolubilityCyanidePhase (matter)Organic chemistry

Abstract

fetched live from OpenAlex

An efficient Pd(0)-catalyzed synthesis of 2-cyanoindoles from 2- gem -dihalovinylanilines is reported. Few methods have aimed to synthesize these scaffolds, which are found in many natural products and have high bioactivity. This protocol features a robust catalyst system utilizing Zn(TFA) 2 to prolong the catalytic activity. Additionally, the amount of cyanide in the reaction phase is minimized by taking advantage of the solubility of Zn(CN) 2 in a two-solvent mixture.

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)0.000
metaresearch head score (Gemma)0.002
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesInsufficient 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 score0.993

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.002
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 integrity0.0000.000
Insufficient payload (model declined to judge)0.0080.000

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 head0.018
GPT teacher head0.252
Teacher spread0.234 · 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

Citations38
Published2017
Admission routes2
Has abstractyes

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