Palladium–imidazolium-catalyzed carbonylative coupling of aryl diazonium ions and aryl boronic acids

✍ Scribed by Merritt B. Andrus; Yudao Ma; Yunfu Zang; Chun Song

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 209 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02186-x

✦ Synopsis

Palladium(II) acetate and N, N-bis-(2,6-diisopropylphenyl)dihydroimidazolium chloride (2 mol%) were used to catalyze the carbonylative coupling of aryl diazonium tetrafluoroborate salts and aryl boronic acids to form aryl ketones. Optimal conditions include carbon monoxide (1 atm) in 1,4-dioxane at 100°C for 5 h. Yields for unsymmetrical aryl ketones ranged from 76 to 90% for isolated materials with only minor amounts of biaryl coupling product observed (2-12%).