Copper‐Catalyzed Synthesis of C‐2 Substituted Indolin‐3‐Ones and Indolin‐3‐One [4+2] Cycloadducts Through Azide‐Tethered Iodonium Ylides
Bibliographic record
Abstract
Abstract In recent years iodonium ylides have gained popularity as versatile metallocarbene precursors, functioning as alternatives to sensitive and potentially toxic diazo compounds. However, their application in metallocarbene‐mediated heterocycle construction has been limited. Herein, we describe a strategy for the synthesis of C‐2 substituted indolin‐3‐ones using azide‐tethered iodonium ylides as metallocarbene precursors under copper catalysis. The formation of an electrophilic C‐acylimine intermediate allows the addition of a broad spectrum of nucleophiles, as well as electron‐rich and unactivated dienes, furnishing highly substituted indolin‐3‐ones and indolen‐3‐one [4+2] cycloadducts. The remarkably short reaction times, high yields, mild conditions, and scalability render this methodology attractive for the synthesis of new scaffolds in drug discovery.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| 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 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| 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 source (direct Gemma or distilled Codex), 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".