One‐Pot Sequential Kumada–Tamao–Corriu Couplings of (Hetero)Aryl Polyhalides in the Presence of Grignard‐Sensitive Functional Groups Using Pd‐PEPPSI‐IPent<sup>Cl</sup>
Bibliographic record
Abstract
Abstract We report a general and rapid chemoselective Kumada–Tamao–Corriu (KTC) cross‐coupling of aryl bromides in the presence of chlorides or triflates with functionalized Grignard reagents at 0 °C in 15 min by using Pd‐PEPPSI‐IPent Cl ( C4 ). Nucleophiles and electrophiles (or both) can contain Grignard‐sensitive functional groups (‐CN, ‐COOR, etc.). Control experiments together with DFT calculations suggest that transmetallation is rate limiting for the selective cross‐coupling of Br in the presence of Cl/OTf with functionalized Grignard reagents. One‐pot sequential KTC/KTC cross‐couplings with bromo–chloro arenes have been demonstrated for the first time. We also report the one‐pot sequential KTC/Negishi cross‐couplings using C4 showcasing the versatility of this methodology.
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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 | 0.001 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| 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".