Cobalt- and Iron-Catalyzed Isomerization–Hydroboration of Branched Alkenes: Terminal Hydroboration with Pinacolborane and 1,3,2-Diazaborolanes
Bibliographic record
Abstract
The synthesis and characterization of a series of structurally varied N -phosphinoamidinate-ligated cobalt complexes is described, along with the successful application of these and a related iron complex as precatalysts in the isomerization–hydroboration of terminal, geminal, and internal alkenes. These reactions proceed under mild conditions (23–65 °C), at relatively low base-metal loadings (1–5 mol %), typically without cosolvent, and with high terminal hydroboration selectivity across a broad spectrum of branched alkenes. With some of the alkene substrates examined, the N -phosphinoamidinate-ligated precatalysts employed herein are shown to provide alternative terminal selectivity versus other previously reported precatalyst classes for such transformations. Reports of terminal-selective metal-catalyzed alkene isomerization–hydroboration disclosed thus far in the literature employ pinacolborane (HBPin); while effective in the system herein, we also report the first examples of such transformations employing either 1,3-dimethyl-1,3-diaza-2-boracyclopentane or benzo-1,3,2-diazaborolane. The application of these 1,3,2-diazaborolanes in place of HBPin in some instances enables novel terminal selectivity in the isomerization–hydroboration of branched alkenes.
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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 | 0.000 |
| 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 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".