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Record W4415732314 · doi:10.1021/acscatal.5c06487

The Regioselective and Diastereoselective Direct Addition of Amines to Alkenes Using a Tantalum-Ureate Hydroaminoalkylation Catalyst

2025· article· en· W4415732314 on OpenAlexafffund
Cameron H. M. Zheng, M. THOMPSON, Rebecca C. DiPucchio, Laurel L. Schafer

Bibliographic record

VenueACS Catalysis · 2025
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsUniversity of British Columbia
FundersNatural Sciences and Engineering Research Council of CanadaUniversity of British ColumbiaCanada Research Chairs
KeywordsRegioselectivityCatalysisGeminalSubstrate (aquarium)Ligand (biochemistry)Conjugated systemHomogeneous catalysis

Abstract

fetched live from OpenAlex

High Resolution Image Download MS PowerPoint Slide An organometallic tantalum catalyst equipped with a ureate ligand achieves the atom-economic hydroaminoalkylation (HAA) reaction to regioselectively form Csp 3 –Csp 3 bonds by adding C–H activated unprotected secondary amines across alkenes. The substrate scope of this catalyst includes a range of activated, unactivated, and conjugated terminal, geminal and internal alkenes with aromatic, aliphatic and N-heterocyclic amines. This broad diversity of compatible substrates illustrates that hydroaminoalkylation offers a useful solution to the longstanding challenge of identifying a general catalyst for directly and catalytically adding amines to alkenes. This catalyst mediates hydroaminoalkylation with controlled regioselectivity and also achieves the challenging dialkylation of select amines with superb diastereoselectivity, including the selective trans -dialkylation of N-heterocycles.

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 categoriesnone
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 score0.062
Threshold uncertainty score0.775

Codex and Gemma teacher scores by category

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

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 head0.015
GPT teacher head0.282
Teacher spread0.267 · 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.

The models applied no category: nothing in the taxonomy fit this work.
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

Citations1
Published2025
Admission routes2
Has abstractyes

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