Synthesis of Carbocyclic Compounds via a Nickel-Catalyzed Carboiodination Reaction
Bibliographic record
Abstract
A scalable nickel-catalyzed carboiodination reaction generating 6-membered carbocycles is reported. NiI2 and P(OEt)3, as the ligand and reducing agent, provided decorated iodo-tetrahydronaphthalenes in up to 94% yield. The impact of varying electronic and steric parameters on the reaction are reported and a non-linear Hammett plot was obtained, supporting a change in the rate-determining step from oxidative addition to reductive elimination. Experimental and DFT studies suggest that the malonate group may stabilize a nickel oxidative-addition complex. A variety of heteroatom-containing nucleophiles and medicinally relevant heterocycles were easily incorporated into the products via simple SN2 chemistry.
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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 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| 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".