A mild, large-scale synthesis of 1,3-cyclooctanedione: expanding access to difluorinated cyclooctyne for copper-free click chemistry

✍ Scribed by Evan A. Sims; Cole A. DeForest; Kristi S. Anseth

• Publisher: Elsevier Science
• Year: 2011
• Tongue: French
• Weight: 264 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2011.02.029

✦ Synopsis

We report the large-scale synthesis of 1,3-cyclooctanedione in five steps with 29% yield. This molecule is a synthetic precursor to difluorinated cyclooctyne, which participates in a bioorthogonal copper-free click reaction with azides. The final step demonstrates the first successful application of the Wacker-Tsuji oxidation to form a cyclic 1,3-dione.