Tantalum Catalyzed Hydroaminoalkylation Enables a Telescoping Catalytic Reaction Sequence for the Synthesis of Benzoannulated Indolizidines and Quinolizidines
Bibliographic record
Abstract
The synthesis of benzoannulated indolizidines and quinolizidines is described through a telescoping reaction sequence featuring hydroaminoalkylation and nickel-catalyzed C–N bond coupling. An in situ generated tantalum (V) ureate catalyst is used to form new Csp 3 ─Csp 3 bonds between saturated N -heterocycles and ortho -chlorostyrene enabled by the α C─H bond activation of the amine. The addition of a nickel C─N coupling catalyst generated from Ni(COD) 2 and DPPF to the reaction mixture allowed for cyclization. Our method leverages the regiodivergent branched and linear products accessed from N -heterocycle and styrene combinations, which are uniquely achieved by our tantalum catalyst to produce new N -heterocycle framework derivatives. Total isolated overall yields of up to 86% were achieved in a single pot. These advances highlight alternative bond disconnections that enable direct access to distinct new N -heterocycle derivatives through early transition metal catalyzed hydroaminoalkylation.
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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 | 0.001 |
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".