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Record W4403213785 · doi:10.1021/acscatal.4c05021

Synthesis of α-Quaternary Aldehydes via a Dual Ni/Rh-Catalyzed Tandem Isomerization–Propargylation Reaction

2024· article· en· W4403213785 on OpenAlexafffund
Justin Ching, Megan Jaschinski, Eun Seo Choi, Mark Lautens

Bibliographic record

VenueACS Catalysis · 2024
Typearticle
Languageen
FieldChemistry
TopicCatalytic Alkyne Reactions
Canadian institutionsUniversity of Toronto
FundersNatural Sciences and Engineering Research Council of CanadaKennarshoreUniversity of Toronto
KeywordsIsomerizationCatalysisTandemChemistryCascade reactionCombinatorial chemistryNickelDual (grammatical number)Organic chemistryMaterials science

Abstract

fetched live from OpenAlex

A dual Ni/Rh catalysis sequence toward α-quaternary aldehydes is reported. An intramolecular approach from allyl propargyl carbonates alongside the intermolecular transformation from allylic alcohols and propargyl carbonates is described. Initial decarboxylative oxidative addition into the propargyl group by nickel generates the electrophilic Ni–allenyl species, and the resulting allylic alkoxide is isomerized into the nucleophilic Rh–enolate species. Upon recombination, the α-propargylated aldehyde is obtained. Preliminary enantioselective results are reported, with varying protocols using either a dual metal single ligand or a dual metal dual ligand system.

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)0.000
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 score0.030
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

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

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 head0.241
Teacher spread0.230 · 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

Citations4
Published2024
Admission routes2
Has abstractyes

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