Ni-Catalyzed Traceless, Directed C3-Selective C–H Borylation of Indoles
Bibliographic record
Abstract
A highly efficient and general protocol for traceless, directed C3-selective C–H borylation of indoles with [Ni(IMes) 2 ] as the catalyst is reported. Activation and borylation of N–H bonds by [Ni(IMes) 2 ] is essential to install a Bpin moiety at the N-position as a traceless directing group, which enables the C3-selective borylation of C–H bonds. The N-Bpin group which is formed is easily converted in situ back to an N–H group by the oxidative addition product of [Ni(IMes) 2 ] and in situ -generated HBpin. The catalytic reactions are operationally simple, allowing borylation of a variety of substituted indoles with B 2 pin 2 in excellent yields and with high selectivity. The C–H borylation can be followed by Suzuki–Miyaura cross-coupling of the C-borylated indoles in an overall two-step, one-pot process providing an efficient method for synthesizing C3-functionalized heteroarenes.
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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) | 0.001 | 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 | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| 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".