Abstract
We demonstrate catalytic organic synthesis by Resonant Acoustic Mixing (RAM): a mechanochemical methodology that does not require bulk solvent or milling media. Using as model reactions ruthenium-catalyzed ring-closing metathesis and copper-catalyzed sulfonamide-isocyanate coupling, RAM mechanosynthesis is shown to be faster, operationally simpler than conventional ball-milling, while also providing the first example of a mechanochemical strategy for ruthenium-catalyzed ene-yne metathesis. Reactions by RAM are readily and directly scaled-up without any significant changes in reaction conditions, as shown by the straightforward 200-fold scaling-up of the synthesis of the antidiabetic drug Tolbutamide, from hundreds of milligrams directly to 30 grams.
| Original language | English |
|---|---|
| Article number | e202115030 |
| Number of pages | 8 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 61 |
| Issue number | 13 |
| Early online date | 20 Jan 2022 |
| DOIs | |
| Publication status | Published - 21 Mar 2022 |
Bibliographical note
Funding Information:We thank the support of the NSERC Discovery Grant (RGPIN‐2017‐06467); NSERC Discovery Accelerator (RGPAS 507837‐17); Tier‐1 Canada Research Chair Program (to T.F.); NSERC PGS‐D Scholarship (to J.L.D.); NSERC CGS‐D (to C.B.L.).
Publisher Copyright:
© 2022 Wiley-VCH GmbH
Keywords
- Acoustic Mixing
- Catalysis
- Green Chemistry
- Mechanochemistry
- Pharmaceuticals
ASJC Scopus subject areas
- Catalysis
- General Chemistry