Comparison of Imine to Olefin Insertion Reactions: Generation of Five- and Six-Membered Lactams via a Nickel-Mediated CO, Olefin, CO, Imine Insertion Cascade
Bibliographic record
Abstract
Cationic nickel complexes of the form L 2 Ni(CH 3 )(RN═C(H)R) + (L 2 = bidentate nitrogen donor) have been probed for their ability to mediate olefin and imine migratory insertion reactions. While these complexes do not undergo alkene insertion into the nickel−methyl bond, the use of olefin-tethered imines CH 2 ═CH(CH 2 ) n N═C(R)aryl ( n = 1−3; R = H, methyl, phenyl) and the addition of CO initiates competitive olefin and imine insertion into the in situ generated nickel−acyl complex. The insertion selectivity shows clear steric and electronic influences and suggests that strong imine coordination can allow it to compete with the more rapid insertion of alkenes. This reactivity has been employed to develop a CO/alkene/CO/imine insertion cascade to synthesize five- and six-membered-ring lactams.
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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) | 0.001 | 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".