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Record W4281381966 · doi:10.1021/acs.orglett.2c01382

Palladium-Catalyzed Three-Component Dearomatization/Sulfonylation Cascade

2022· article· en· W4281381966 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueOrganic Letters · 2022
Typearticle
Languageen
FieldChemistry
TopicSulfur-Based Synthesis Techniques
Canadian institutionsUniversity of Toronto
FundersNatural Sciences and Engineering Research Council of CanadaKennarshoreUniversity of TorontoDeutsche Forschungsgemeinschaft
KeywordsChemistryIndolineArylPalladiumCatalysisElectrophileIodideIndole testCombinatorial chemistryComponent (thermodynamics)Organic chemistryAlkyl

Abstract

fetched live from OpenAlex

The diastereoselective synthesis of sulfonylated indolines is reported. A palladium-catalyzed dearomative sulfination of (aza)indole-tethered aryl iodides generates reactive benzylic sulfinates. These intermediates react with electrophiles in a one-pot, two-step process to generate sulfonylated products in good yields and excellent diastereoselectivity. This three-component sequence demonstrates good scalability and can be applied toward the synthesis of sulfonamides. Additionally, further derivatizations of aryl iodide containing products furnish spiro- and alkynylated indoline products.

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.

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)0.000
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 score0.010
Threshold uncertainty score0.991

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
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 science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0100.000

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 head0.011
GPT teacher head0.210
Teacher spread0.199 · 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