Pd‐Catalyzed Sonogashira Cross‐Coupling Reactions of <i>gem</i>‐Dibromovinyl BODIPY Derivatives
Bibliographic record
Abstract
Abstract 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐ s ‐indacene (BODIPY) derivatives bearing gem ‐dibromovinyl moieties at either the β‐ or α‐positions of the pyrrole rings, directly or through phenyl spacers, undergo efficiently Sonogashira and Stille Pd‐catalyzed cross‐coupling. The structures of the resulting 1,1‐diynyl‐1‐alkene and 1,1‐diphenyl‐1‐alkene products were assigned using MS, NMR and in some cases X‐ray diffraction analysis. 1,1‐Diynyl‐1‐alkene BODIPYs exhibit red shifted absorption maxima, particularly when substituents were introduced at the α‐position rather than the β‐position of the pyrrole ring. Aromatic compounds showed larger red shifts as compared to the aliphatic substituted analogs. The highest red shifts were observed with compounds featuring electron donating substituents. Spectroscopic properties of α‐substituted 1,1‐diynyl‐ p ‐N,N‐dimethylaminophenyl‐1‐alkenes are sensitive to protonation resulting in remarkable pH‐responsive changes in the absorption and fluorescence emission spectra.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot 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.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| 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) | 0.001 | 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 source (direct Gemma or distilled Codex), 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".