Palladium catalyzed arylation of N-alkyl O-allyl carbamates: Synthesis of cinnamyl alcohols via Heck arylation

✍ Scribed by Keiji Ono; Keigo Fugami; Shuji Tanaka; Yoshinao Tamaru

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 269 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)73132-7

✦ Synopsis

N-Alkyl O-cinnamyl carbamates (3) were prepared in good yields by palladium cat-'alyzed arylation of N-alkyl O-ally1 carbamak s (2) with aryl iodides. Heck type arylation of allylic alcohols with aromatic1 and IWemammatic halides2 is an efficient entry to the preparation of aromatic-substituted alkyl aldehydes and ketones (eq I). Jefferys recently reported that the similar reaction, in the presence of a stoichiometric amount of silver acetates, altered the course of the reaction, providing cinnamyl alcohols in synthetically useful yields (eq 2, XY = H). Based on the sele.ctive formation of a,~,y,&unsaturated alcohols by the reaction of ally1 alcohols with either vinyl triflates4 or vinyl iodide in the