Synthesis of 2,4- and 2,5-Disubstituted Oxazoles via Metal- Catalyzed Cross-Coupling Reactions
✍ Scribed by Carla M. Counceller; Chad C. Eichman; Nicolas Proust; James P. Stambuli
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- English
- Weight
- 180 KB
- Volume
- 353
- Category
- Article
- ISSN
- 1615-4150
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✦ Synopsis
Abstract
The rapid synthesis of 2,4‐ and 2,5‐disubstituted oxazoles via metal‐catalyzed cross‐coupling reactions is reported. The 4‐ or 5‐position of the corresponding 4‐ or 5‐halogenated 2‐butylthiooxazoles was successfully functionalized via Suzuki–Miyaura, Sonogashira and Stille cross‐coupling reactions. The 2‐position of the 2‐butylthiooxazoles obtained was further coupled to various organozinc reagents through palladium‐ or nickel‐mediated cross‐coupling reactions.
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## Abstract The iodine‐catalyzed process allows the synthesis of oxazoles (24 examples) from hydrochloride (I) and aldehydes under mild conditions.