Metal‐Free Transfer C−H Borylation of Substituted Thiophenes
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Bibliographic record
Abstract
Abstract Thiophenes are crucial chemical building blocks in the fields of medicinal and material chemistry. As such, the C−H functionalization of these units is of key importance for developing novel applications. Herein, we report the C−H borylation of thiophenes using metal‐free transfer C−H borylation. When performed on C2‐substituted thiophenes, the reaction is selective for the borylation on C5, while C3‐substituted thiophenes are borylated on C2, a complementary selectivity from reported C−H borylation approaches that typically prefer to borylate at the C5 position. An optimization of the catalytic system was performed. The reaction was shown to work with electronically diverse thiophenes and was also compatible with sensitive functional groups. Computational investigation of the reaction mechanism suggests a Lewis pair C−H activation mechanism with a selectivity that is kinetically driven. The methodology developed herein is an economical pathway for the preparation of C2‐borylated C3‐substituted thiophenes.
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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 | 0.001 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.002 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.006 | 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 it