Rhodium-catalyzed ring-opening reactions of heterobicyclic akenes with heteroarene nucleophiles: an experimental and computational investigation
Bibliographic record
Abstract
We present an experimental and computational investigation into the rhodium-catalyzed ring-opening reactions of heterobicyclic alkenes with heteroarene nucleophiles. The reaction provides a facile route to trans-substituted dihydronaphthalen-1-ol and 1-amino-dihydronaphthalene products in up to a 95% yield as a single diastereomer. This reaction is 100% atom-economic and offers C–C bond formation without prior functionalization of the coupling partners. The mechanism and origins of selectivity were probed with density functional theory (DFT) at the MN15/Def2-TZVPP level of theory. The energetic barriers between iridium- and rhodium-catalyzed pathways were compared via DFT. Additionally, the reactivity and energetic barriers across diverse heterobicyclic alkenes and heteroarenes were calculated to unveil their relative reactivity.
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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 | 0.000 | 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 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".