Transition Metal‐Catalyzed Cross‐Couplings of Benzylic Sulfone Derivatives
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Bibliographic record
Abstract
Abstract In recent years, the use of organosulfones as a new class of cross‐coupling partner in transition‐metal catalyzed reactions has undergone significant advancement. In this personal account, our recent investigations into desulfonylative cross‐coupling reactions of benzylic sulfone derivatives catalyzed by Pd, Ni, and Cu catalysis is described. Combined with the facile α‐functionalizations of sulfones, our methods can be used to form valuable multiply‐arylated structures such as di‐, tri‐, and, tetraarylmethanes from readily available substrates. The reactivity of sulfones can be increased by introducing electron‐withdrawing substituents such as 3,5‐bis(trifluoromethyl)phenyl and trifluoromethyl groups, which enable more challenging cross‐coupling reactions. Reactive intermediates including Cu‐carbene complexes were identified as key intermediates in sulfone activation, representing new types of C−SO 2 bond activation processes. These results indicate sulfones are powerful functional groups, enabling new catalytic desulfonylative transformations.
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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 | 0.001 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.003 | 0.001 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 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