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Record W4397023410 · doi:10.1021/acssuschemeng.4c02486

A Sustainable Access Route to Carbazoles via C–H/C–H Oxidative Functionalization/Cyclization of Arylamines

2024· article· en· W4397023410 on OpenAlexafffund
Giulia Brufani, Shaomin Chen, Benedetta Di Erasmo, Anastasiia M. Afanasenko, Yanlong Gu, Chao‐Jun Li, Luigi Vaccaro

Bibliographic record

VenueACS Sustainable Chemistry & Engineering · 2024
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsMcGill UniversityCentre in Green Chemistry and Catalysis
FundersFonds de recherche du Québec – Nature et technologiesCanada Research ChairsNatural Sciences and Engineering Research Council of CanadaEuropean CommissionChina Scholarship CouncilCanada Foundation for InnovationIstituto Nazionale Previdenza Sociale
KeywordsCarbazoleIntramolecular forceOxidative coupling of methaneCombinatorial chemistryChemistryCatalysisSurface modificationMoleculeMolecular oxygenOxidative phosphorylationOrganic chemistry

Abstract

fetched live from OpenAlex

Carbazole is an important structural motif found in natural products and active pharmaceutical ingredients. In addition, the special optoelectronic properties shown by this class of molecules have led to interesting applications in the field of material science. Given the potential of this N -heterocycle system, we have searched for a novel and more sustainable methodology for their preparation. Herein, we report a novel protocol based on a heterogeneous Pd-catalyzed intramolecular oxidative C–H/C–H coupling methodology, allowing access to carbazoles from variously functionalized diarylamines and triarylamines. Optimal results could be achieved using Pd/C as a heterogeneous catalyst in combination with molecular oxygen at atmospheric pressure. This newly developed methodology allows the facile and clean synthesis of structurally diverse carbazoles, including both natural products and light-emitting molecular entities.

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)0.001
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: none
Teacher disagreement score0.657
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.002
Science and technology studies0.0000.000
Scholarly communication0.0000.001
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0020.000

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 head0.009
GPT teacher head0.260
Teacher spread0.251 · 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

Citations15
Published2024
Admission routes2
Has abstractyes

Explore more

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