Organoboron Catalysis as a Strategy for the Regioselective Functionalization of Ambident Nitrogen Heterocycles
Bibliographic record
Abstract
Controlling regioselectivity in synthetic transformations of ambident nitrogen heterocycles is a growing field of research. N-Functionalized heterocycles bearing an exocyclic oxygen atom and one or more ring nitrogen atoms are prevalent in structures of novel pharmaceutical agents. The competing N and O-functionalization can be problematic in the synthesis of said agents. This thesis describes the development of a methodology for regioselective access to N-allylated tautomerizable heteroarenes via synergistic organoboron/palladium catalysis. Regioselective installation of an allyl group at a specific heteroatom on a heterocycle is desirable due to its synthetic utility, behaving as a useful entry point to introduce complex substituents via further synthetic transformations. In contrast to methods employing allyl esters or allylic carbonates, high atom economy is achieved employing allylic alcohols as reaction partners, producing water as the sole by-product. High yields are obtained in the regioselective N-allylation of a plethora of heterocycles with various substituted allylic alcohols.
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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".