Scope and advances in the catalytic propargylic substitution reaction
Why this work is in the frame
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Bibliographic record
Abstract
Nucleophilic displacement of the propargylic alcohol is one of the sought-after methods in the current scenario. The highly nucleophilic alkyne functional moiety along with its considerably acidic terminal hydrogen atom allows the propargylic unit to play a crucial role in organic synthesis by offering a handle for further synthetic transformations. Until 2000, the most fundamental propargylic substitution reaction was the Nicolas reaction, a multi-step transformation, developed in 1972, which involved cobalt as a stoichiometric promoter. Therefore, the direct catalytic substitution of propargylic alcohols was a highly desirable method for development. The pioneering work on the Ru-catalyzed propargylic substitution reaction in 2000 encouraged many researchers to develop several novel catalytic propargylic substitution reactions, which have made rapid progress since then. The purpose of this review is to emphasise the involvement of diverse types of Lewis acid, transition metal and Brønsted acid catalysts in the propargylic substitution reaction and provide an updated summary of the recent developments in this field. The selected examples presented here are the most significant and relevant ones and we believe that this will help the readers to comprehend the scope of the propargylic substitution reaction with diverse types of catalysts and will envisage the scientific community for the future developments in this field.
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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 | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| 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 it