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Record W2968806475 · doi:10.1039/c9dt02756d

Trace water affects tris(pentafluorophenyl)borane catalytic activity in the Piers–Rubinsztajn reaction

2019· article· en· W2968806475 on OpenAlexafffund
Alyssa F. Schneider, Yang Chen, Michael A. Brook

Bibliographic record

VenueDalton Transactions · 2019
Typearticle
Languageen
FieldChemistry
TopicOrganoboron and organosilicon chemistry
Canadian institutionsMcMaster University
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsBoraneTrisTRACE (psycholinguistics)ChemistryCatalysisPhotochemistryMedicinal chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Improved methods to control silicone synthesis are required due to the sensitivity of siloxane bonds to acid/base-mediated chain redistribution/depolymerization. The Piers-Rubinsztajn reaction employs tris(pentafluorophenyl)borane as an efficient catalyst (<0.1 mol%) for siloxane bond formation from hydro- and alkoxysilanes - typical reactions proceed in open flasks at room temperature within minutes. While advantageous under ideal conditions, the boron catalyst activity may be affected by age, storage conditions and various environmental factors, particularly humidity. Under conditions of high humidity it may be necessary to apply heat and/or use increased catalyst loading in the reactions; there is often an induction time. We examine induction times in the Piers-Rubinsztajn reaction as a function of water concentrations in the reagent or catalyst solution and show that water in the reagent solution or atmosphere is less problematic than water found in the catalyst stock solution. A relatively linear increase in induction time accompanied higher water concentrations in the catalyst solution - no such effect was observed when the water was in the reagent solution. Reaction rates in both scenarios were similar, i.e., not affected by the induction time. Improvements in the stability of catalyst solutions were observed when B(C6F5)3 was stored in low molecular weight silicone oils, and pre-complexed with HSi(OSiMe3)3. These outcomes are ascribed to the ability of HSi groups to outcompete water in binding with B(C6F5)3 to initiate reaction, unless the boron is pre-complexed with water.

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 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 score0.007
Threshold uncertainty score0.997

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 integrity0.0000.001
Insufficient payload (model declined to judge)0.0040.001

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 head0.009
GPT teacher head0.225
Teacher spread0.217 · 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

Citations29
Published2019
Admission routes2
Has abstractyes

Explore more

Same venueDalton TransactionsSame topicOrganoboron and organosilicon chemistryFrench-language works237,207