Direct Carboboration of Aryl Alkenes with Stable Organoborons Through Ziegler‐Type Addition
Bibliographic record
Abstract
Carbometallation reaction represents a classic strategy for the bifunctionalization of unsaturated hydrocarbons, yet conventional implementations predominantly rely on either highly reactive organometallic reagents or transition metal catalysts. Notably, the direct employment of metalloid organoboron reagents for such addition processes remains elusive except when specific substrate combinations are employed. Herein, a base-catalyzed carboboration reaction of aryl alkenes with bench-stable benzylic boronates is reported. This anionic-based strategy is not only applicable to the carboboration of substituted styrenes but also to vinyl cyclopropanes and vinyl cyclobutane, affording the corresponding 1,5- and 1,6-carboboration-related products. Combined experimental and computational investigations reveal a mechanism that involves the Ziegler-type carbometallation process. The synthetic utility is further highlighted by the facile one-pot derivatization of the resulting benzylic boronates. Furthermore, a modified catalytic system offers an alternative to the anionic polymerization of styrene.
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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) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.001 |
| 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".