1999 alkylation, arylation, dealkylation, dearylation, C-acylation, olefination

alkylation, arylation, dealkylation, dearylation, C-acylation, olefinationO 0280

22 - 061Palladium-Catalyzed Alkylation with Allylic Acetates under NeutralConditions. — The palladium-catalyzed allylation of various nucleophileswith cinnamyl acetate (II) either in the presence of BSA/AcOK catalyst system(method A) or under base-free conditions (method B) is studied. Whereasnitro compounds (I) are only allylated by method B, nucleophiles (Va)-(Vd) areallylated by either method to give mono or diallylated products. The exclusiveformation of diallylated nucleophiles is observed for Meldrum’s and barbituricacids (VIII) and (X). The allylated product of malonate (Ve) is only formedby method A. — (GIAMBASTIANI, GIULIANO; POLI, GIOVANNI; J. Org.Chem. 63 (1998) 26, 9608-9609; Dip. Chim. Org. Ugo Schiff, Univ. Firenze,I-50121 Firenze, Italy; EN)

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