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Record W2574083107 · doi:10.1021/acscatal.6b03209

Employing Pd-Catalyzed C–H Arylation in Multicomponent-Multicatalyst Reactions (MC)<sup>2</sup>R: One-Pot Synthesis of Dihydrobenzoquinolines

2017· article· en· W2574083107 on OpenAlexafffund
Fabian Lied, Helena Brodnik, Steffen Kress, Bogdan Štefane, Frank Glorius, Mark Lautens

Bibliographic record

VenueACS Catalysis · 2017
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsUniversity of Toronto
FundersH2020 European Research CouncilAlphora ResearchNatural Sciences and Engineering Research Council of CanadaAlfried Krupp von Bohlen und Halbach-StiftungUniversity of TorontoDeutsche Forschungsgemeinschaft
KeywordsCatalysisEnantioselective synthesisChemistryCombinatorial chemistryReaction conditionsOne-pot synthesisOrganic chemistry

Abstract

fetched live from OpenAlex

The one-pot synthesis of a broad variety of dihydrofuroquinolines, dihydrothienoquinolines, and dihydrobenzoquinolines is reported. The combination of the Rh(I)-catalyzed hydroarylation of vinylpyridines with the Pd(0)/Pd(II)-catalyzed direct C–H arylation in a Multicomponent-Multicatalyst Reaction (MC) 2 R could be used to develop an efficient and step-economic protocol for the rapid construction of molecular complexity. A high-yielding synthesis of π-extended heteroarenes through an efficient three-step-one-pot procedure and a highly enantioselective synthesis of 6-alkylsubstituted dihydrobenzoquinolines are shown.

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)0.006
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 score0.040
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.006
Meta-epidemiology (narrow)0.0000.001
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0010.001
Science and technology studies0.0010.000
Scholarly communication0.0000.001
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0010.000

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 head0.044
GPT teacher head0.305
Teacher spread0.261 · 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
Published2017
Admission routes2
Has abstractyes

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