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Record W7132918944

Rhodium-catalyzed coupling reactions of multisubstituted alkenes, arylsubstituted allylic amines, esters and alcohols with arylboronic acids in aqueous media

2003· dissertation· W7132918944 on OpenAlexfundno aff
Andrei Loutchnikov

Bibliographic record

VenueTSpace · 2003
Typedissertation
Language
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsnot available
FundersNatural Sciences and Engineering Research Council of CanadaUniversity of Toronto
KeywordsAllylic rearrangementAqueous mediumCatalysisCoupling reactionReactivity (psychology)Yield (engineering)Phosphine
DOInot available

Abstract

fetched live from OpenAlex

This thesis is divided into three parts. Chapter 1 gives a brief introduction to the recent discoveries of rhodium-catalyzed cross-coupling reactions of alkenes and alkynes with arylboronic acids in aqueous media. The initial investigations on the path to the development of an asymmetric rhodium-catalyzed coupling reaction between multisubstituted alkenes and arylboronic acids are presented in Chapter 2. Multisubstituted alkenes were to be less reactive than monoarylsubstituted ethylenes, giving low or no yield of the desired coupling products. A procedure was developed, which allowed us to overcome the problem of poor reactivity for several of the substrates. A rhodium(I) species catalyzed the coupling reaction between pyridylsubstituted alkenes and o-tolylboronic acid in water when phosphine ligands were not included in the reaction mixture. Chapter 3 describes the first examples of several novel rhodium-catalyzed allylic arylation reactions. The substrates which reacted with arylboronic acids in presence of a rhodium catalyst include: (a) allylic amines; (b) arylsubstituted allylic esters; (c) arylsubstituted allylic alcohols.

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)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Research integrity
Consensus categoriesMeta-epidemiology (narrow)
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 score0.090
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0020.002
Meta-epidemiology (broad)0.0020.000
Bibliometrics0.0010.002
Science and technology studies0.0010.001
Scholarly communication0.0000.001
Open science0.0010.000
Research integrity0.0020.002
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 head0.019
GPT teacher head0.307
Teacher spread0.288 · 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; both teacher heads agree on what is shown here.

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

Citations0
Published2003
Admission routes1
Has abstractyes

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