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Record W3138163353 · doi:10.1039/d1ob00520k

The synthesis, properties, and reactivity of Lewis acidic aminoboranes

2021· article· en· W3138163353 on OpenAlexafffund
Jordan N. Bentley, Selvyn A. Simoes, Ekadashi Pradhan, Tao Zeng, Christopher B. Caputo

Bibliographic record

VenueOrganic & Biomolecular Chemistry · 2021
Typearticle
Languageen
FieldChemistry
TopicOrganoboron and organosilicon chemistry
Canadian institutionsYork UniversityToronto Public Health
FundersNatural Sciences and Engineering Research Council of CanadaCanada Research ChairsCanada Foundation for InnovationYork University
KeywordsChemistryLewis acids and basesSubstituentReactivity (psychology)Medicinal chemistryStereochemistryOrganic chemistryComputational chemistryCatalysis

Abstract

fetched live from OpenAlex

The evolution of frustrated Lewis pair chemistry has led to significant research into the development of new Lewis acidic boranes. Much of this has focused on modifying aryl substituents rather than introducing heteroatoms bound to boron. We recently reported that bis(pentafluorophenyl)phenothiazylborane (1) could be used as a Lewis acid catalyst for the heterolytic dehydrocoupling of stannanes. In this work, we synthesize and characterize a family of Lewis acidic aminoboranes and explored their reactivity with various Lewis bases as well as their efficacy as catalysts for stannane dehydrocoupling and hydrosilylation. Quantum chemical calculations were undertaken to understand the origins of the Lewis acidity and the most Lewis acidic aminoborane (5) was found to be an effective catalyst even in coordinating solvents such as water or acetonitrile, suggesting the amino substituent provides a level of protection against competing donors.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation 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 score0.001
Threshold uncertainty score0.002

Distilled classifier scores by category (both heads)

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)0.0010.000

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 head0.199
Teacher spread0.188 · 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 source (direct Gemma or distilled Codex), 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

Citations6
Published2021
Admission routes2
Has abstractyes

Explore more

Same venueOrganic & Biomolecular ChemistrySame topicOrganoboron and organosilicon chemistryFrench-language works237,207