Platinum-Catalyzed Formation of Quinolines from Anilines. Aliphatic α-C−H Activation of Alkylamines and Aromatic <i>o</i><i>rtho-</i>C−H Activation of Anilines
Bibliographic record
Abstract
Platinum(II) bromide catalyzes the reaction of aniline with n -Bu 3 N to give N -butylaniline and 2-propyl-3-ethylquinoline. The formation of the quinoline derivative is strongly favored (TON up to 40) by the presence of both n -Bu 4 PBr and 1-hexene. The same reaction products are formed by reaction of aniline with either n -Bu 2 NH or n -BuNH 2 (PtBr 2 catalyst). Under similar experimental conditions, the “PtBr 2 − n -Bu 4 PBr−1-hexene” system catalyzes the transformation of N -hexylaniline into 2-pentyl-3-butylquinoline (TON up to 42). Similarly, N -ethylaniline affords 2-methylquinoline (TON of 22). In both cases, the presence of 1-hexene strongly favors the conversion of the N -alkylaniline. On the basis of both complementary experiments and literature data, these unprecendented results are interpreted by an α-C−H activation of n -Bu 3 N (iminium species as intermediate), leading to N -butylaniline (butyl group transfer to aniline). The “PtBr 2 −n-Bu 4 PBr−1-hexene” system also catalyzes an α-C−H activation of the alkyl part of N -( n -alkyl)anilines to generate the corresponding imines, which dimerize. A heterocyclization then occurs, via a Pt(II)-catalyzed aromatic ortho -C−H activation, followed by deamination and dehydrogenation (1-hexene as hydrogen acceptor). Although not completely clear, the role of an alkene (1-hexene or ethylene) is highlighted.
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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".