Iron-Catalyzed Direct Arylation through an Aryl Radical Transfer Pathway
Bibliographic record
Abstract
All reactions were run under an inert atmosphere (argon) with flamedried glassware using standard techniques for manipulating air-sensitive compounds.Anhydrous solvents were obtained by filtration through drying columns (benzene) or by distillation over sodium and calcium hydride (p-xylene, pyridine).Flash column chromatography was performed using 230-400 mesh silica with the indicated solvent system according to standard techniques.Analytical thin-layer chromatography (TLC) was performed on pre-coated, glass-backed silica gel plates.Visualization of the developed chromatogram was performed by UV absorbance (254 nm) and/or aqueous potassium permanganate.Nuclear magnetic resonance spectra were recorded either on 300 MHz or 400 MHz spectrometers.Chemical shifts for 1 H NMR spectra are recorded in parts per million from tetramethylsilane with the solvent resonance as the internal standard (chloroform, = 7.27 ppm).Data were reported as follows: chemical shift, multiplicity (s = singlet, d = doublet, t = triplet, m = multiplet and br = broad), coupling constant in Hz and integration.Chemical shifts for 13 C NMR spectra were recorded in parts per million from tetramethylsilane using the central peak of deuterochloroform (77.36 ppm) as the internal standard.Preparative High Performance Liquid Chromatography was performed using reverse phase elution on a system equipped with simultaneous diode array UV detection.Data are reported as follows: (column type, eluent, flow rate: retention time (t r )).Low resolution mass spectra were performed either on a GC/MS Agilent 6890 Series GC system equipped with an Agilent 5973 Network-G2578A Standard Turbo EI MSD and/or on an Agilent 1100 Series LC/MSD system equipped with an APCI mass detector with simultaneous diode array UV detection.Reagents: Commercial reagents were used as supplied or purified by standard techniques where necessary.OMe 5a
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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 | 0.001 |
| 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 | 0.001 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.425 | 0.003 |
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; both teacher heads agree on what is shown here.
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".