Metal-Free Catalytic Cross-Coupling of Esters and Boranes
Bibliographic record
Abstract
Over the last 50 years, palladium-catalyzed cross-coupling has become ubiquitous in chemical synthesis from laboratory to commercial scale. Due to the great importance of these reactions, extensive research efforts have been devoted to improving the sustainability, cost, and diversity of the catalysts and coupling partners. Herein, we report the rational design and experimental validation of a metal-free catalyst for cross-coupling of formate esters with organoboranes, forming aldehydes under mild, additive-free conditions. The novel mechanism establishes a model for direct C(acyl)–C(sp2) bond formation, a motif previously inaccessible via metal-free or radical-free cross-coupling pathways. Overall, this boron/nitrogen-based system is found to even outperform the efficacy of state-of-the-art nickel catalysts for ester cross-coupling, demonstrating the utility of main-group catalysts in efficiently activating challenging bonds.
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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 | 0.001 |
| Open science | 0.001 | 0.001 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.004 | 0.002 |
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".