Development and Optimization of Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction of Tertiary Sulfones.
Bibliographic record
Abstract
Suzuki-Miyaura cross-coupling reactions are a popular and useful synthetic method to create new carbon-carbon bonds, due to their relative safety and stability.1 In particular, this method has shown promise in the construction of densely functionalized quaternary carbon stereocenters that can be bulky and otherwise difficult to synthesize, making it optimal for synthesizing pharmaceuticals and natural products.1,2 Tertiary sulfones are a class of compounds that are highly versatile and have demonstrated abilities to serve as unique pseudohalides and electrophilic coupling partners, which allows for added flexibility in this powerful reaction.3 In previous work done by the Crudden group, a variety of benzylic and allylic tertiary sulfones were used to produce quaternary carbon centers, however it required naphthyl or similar p-extended groups in order to facilitate coordination of nickel-catalyzed Suzuki couplings.4 We are currently investigating the possibility of using tertiary sulfones containing conjugated olefins to overcome this limitation. This would further enhance the utility of this reaction, allowing access to synthetically challenging products with a conjugated olefin backbone that can be further functionalized, serving as a versatile lynchpin handle. This work will enable direct and efficient synthesises of natural products and further develop the scope of pharmaceutical compounds. [1] - Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451-3479. [2] - Ling, T.; Garfias, J. M.; Lawson, S. L.; Rivas, F. Tetrahedron. 2025, 183, 134711. [3] - Trost, B. M.; Chem-Eur J. 2019, 25, 11193 – 1121. [4] - Ariki, Z. T.; Maekawa, Y.; Nambo, M.; Crudden, C. M. J. Am. Chem. Soc. 2017, 140 (1), 78–81.
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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 | 0.002 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.001 | 0.001 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.000 | 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".