Palladium-catalyzed ring expansion reaction of 1-alkynylcyclobutanols with aryl iodides: an efficient route to 2-disubstituted methylenecyclopentanones

✍ Scribed by Li-Mei Wei; Li-Lan Wei; Wen-Bin Pan; Ming-Jung Wu

• Book ID: 104252682
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 87 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02581-9

✦ Synopsis

The reaction of 1-alkynylcyclobutanols with aryl iodides in the presence of Pd(OAc) 2 and Et 3 N in acetonitrile at 80°C for 24 h gives 2-disubstituted methylenecyclopentan-1-ones in modest to good yields. The tandem insertion-ring expansion process proceeds via the formation of an alkynyl p-complex, followed by migration of a carbon carbon bond of the tert-alkanol to form the cyclopentanones stereoselectively.