Desulfonylative Suzuki–Miyaura Cross-Coupling of Unactivated Aryl Sulfones through Ni Catalysis
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Bibliographic record
Abstract
We describe a Ni-catalyzed Suzuki–Miyaura cross-coupling of simple aryl sulfones with arylboroxines through carbon–sulfonyl (C–SO 2 ) bond activation. The use of 1,5-cyclooctadiene (cod) as a ligand on Ni is essential in this cross-coupling reaction, affording unsymmetric biaryl products in good yields. The utilization of the sulfonyl moiety as both an electron-withdrawing and directing group provides highly functionalized products via regioselective and iterative transformations, which are difficult to achieve with typical leaving groups, such as aryl halides. Moreover, cyclic aryl sulfones can be employed in ring-opening cross-coupling and subsequent trapping reactions with various electrophiles, producing π-conjugated structures bearing valuable, sulfur-containing functional groups. Competition experiments reveal that the Ni-cod catalyst preferentially promotes the coupling with aryl sulfones over aryl chlorides, which is opposite the conventional reactivity of aryl electrophiles. Additionally, the sodium sulfinate released during C–SO 2 bond cleavage exhibits an unprecedented rate-accelerating effect, which is supported by mechanistic studies, control experiments and density functional theory (DFT) calculations.
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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 | 0.001 |
| Meta-epidemiology (broad) | 0.001 | 0.001 |
| Bibliometrics | 0.000 | 0.002 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
Machine scores (provisional)
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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