Abstract
A metal-free strategy has been developed for the α-arylation of carboxylic acids, secondary amides, and esters employing arenes as key reagents. This process entails the Lewis-acid catalyzed reductive Friedel-Crafts alkylation of arenes utilizing α-ketoacids, facilitated by silane in HFIP solvent. The transformation exhibits exceptional functional group tolerance, enabling late-stage functionalization of natural products. This one-step protocol has been successfully used to synthesize commercially available drugs, such as adiphenine, piperidolate, derivatives of ketoprofen, ibuprofen, flurbiprofen, and the pesticide bromopropylate.
| Original language | English |
|---|---|
| Pages (from-to) | 10688-10691 |
| Number of pages | 4 |
| Journal | Chemical Communications |
| Volume | 60 |
| Issue number | 77 |
| DOIs | |
| State | Published - 2 Sep 2024 |
| Externally published | Yes |
Bibliographical note
Publisher Copyright:© 2024 The Royal Society of Chemistry.
ASJC Scopus subject areas
- Electronic, Optical and Magnetic Materials
- Catalysis
- Ceramics and Composites
- General Chemistry
- Surfaces, Coatings and Films
- Metals and Alloys
- Materials Chemistry
Fingerprint
Dive into the research topics of 'Chemoselective deoxygenative α-arylation of carboxylic acids, amides, and esters: synthesis of anesthetic and anti-inflammatory compounds'. Together they form a unique fingerprint.Cite this
- APA
- Author
- BIBTEX
- Harvard
- Standard
- RIS
- Vancouver