Highly Selective Nickel‐Catalyzed Isomerization‐Hydroboration of Alkenes Affords Terminal Functionalization at Remote C−H Position
Bibliographic record
Abstract
We report herein the synthesis and characterization of nickel complexes supported by tridentate and bidentate phosphino(silyl) ancillary ligands, along with the successful application of these complexes as precatalysts for the hydroboration of terminal and internal alkenes using pinacolborane (HBPin). These reactions proceeded with low nickel loadings of 2.5-5 mol % in the absence of co-solvent, and in some cases at room temperature. Isomerization to afford exclusively the terminal hydroboration product was obtained across a range of internal alkenes, including tri- and tetra-substituted examples. This reactivity is unprecedented for nickel and offers a powerful means of achieving functionalization at a C-H position remote from the C=C double bond. Nickel-catalyzed deuteroboration experiments using DBPin support a mechanism involving 1,2-insertion of the alkene and subsequent chain-walking, which results in isotopic scrambling.
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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".