Nickel-Catalyzed N-Arylation of Sulfinamides: A Comparative Study versus Analogous Sulfonamide Cross-Couplings
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Bibliographic record
Abstract
Despite recent progress regarding the metal-catalyzed C–N cross-coupling of (hetero)aryl (pseudo)halides with NH substrates, such transformations involving sulfinamide nucleophiles are underdeveloped. Herein we report on Ni-catalyzed C–N cross-couplings of this type, employing primarily tert-butanesulfinamide (i.e., Ellman’s sulfinamide) as a test nucleophile. Inexpensive and abundant (hetero)aryl chlorides proved to be suitable reaction partners in such reactions when using (L)Ni(o-tol)Cl (L = CyPAd-DalPhos or PhPAd-DalPhos) precatalysts. We also present results of an experimental and computational study focusing on C–N reductive elimination involving newly prepared and isolated sulfinamido (L)Ni(o-tol)(NHS(O)tBu) complexes, in which deprotonation leading to the formation of the putative anionic nitrene species [(L)Ni(o-tol)(NS(O)tBu)]− represents the preferred pathway for C–N reductive elimination, in keeping with our past study of related sulfonamido complexes.
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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 | 0.001 | 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 | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.004 | 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