Palladium-Catalyzed Stille-Type Coupling of <i>N</i>-Acyl Iminium Ions with Distannanes: A Multicomponent Synthesis of α-Amidostannanes
Bibliographic record
Abstract
High Resolution Image Download MS PowerPoint Slide The palladium-catalyzed three-component coupling of imines, acid chlorides, and hexabutyldistannane is described. This results in the synthesis of various α-amidostannanes in good yields, without the use of strong nucleophilic organometallic reagents. The reaction is believed to proceed via a Stille-type cross coupling of an in situ -generated N -acyl iminium salt with Bu 3 SnSnBu 3 and reaches completion within 1 h at ambient temperature using simple, unligated Pd 2 dba 3 as a catalyst. Combining the formation of α-amidostannanes with lithiation and carboxylation allows the overall synthesis of amino acid derivatives in two steps from imines, acid chlorides, and CO 2 .
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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 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| 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".