Palladium-catalysed synthesis of allyl acetates from allenes

✍ Scribed by Suren Husinec; Milka Jadranin; Rade Markovic; Milos Petkovic; Vladimir Savic; Nina Todorovic

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 877 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.05.136

✦ Synopsis

Allyl acetates were synthesised from allenes utilising methodology based on the general reactivity of p-allyl palladium intermediates which participate efficiently in transformations involving nucleophiles.

Reactions of allenes and aryl iodides in the presence of AcONa and Pd(OAc) 2 /PPh 3 as the catalytic system afforded allyl acetates in moderate to good yields. Monosubstituted allenes, depending on their structure, produced either a separable mixture of two regioisomeric products or a single regioisomer. As allylic acetates can be easily hydrolysed, the methodology is applicable for the synthesis of allyl alcohols as well.