Evaluation of H <sub>2</sub> O <sub>2</sub> /HFIP as a convenient sulfoxidation reagent for boronate containing thioethers
Bibliographic record
Abstract
It is recognized that boronic acid derivatives are often sensitive to common sulfur oxidizing reagents. In this paper the value of the H 2 O 2 /HFIP combination as a viable thioether (sulfide) monoxidation reagent is demonstrated, with the reagent system providing sulfoxide while in many cases leaving the boronate functionality unperturbed. Bpin bearing sulfides were converted to sulfoxide in 49%–86% yield, with occasional alcohol side products arising from oxidation at the boron-bearing carbon. Other boronate esters possessing chemical resilience comparable to Bpin were also amenable to the chemistry, with sulfoxides isolated in 66%–96% yield. Less robust boronic acid derivatives such as Bcat and BDan readily succumbed to alcohol conversion. Sulfides containing geminal bis(boronates) were cleanly converted to sulfoxide. The chemical yields and the convenience of this sulfoxidation procedure make this protocol attractive for the oxidation of selected boronate containing thioethers. Dedicated to the memory of Willie Leigh, a friend and mentor.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.002 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
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".