Palladium catalyzed C-allylation of nitroalkanes

Abstract A detailed study of palladium catalyzed C-allylation of aliphatic nitro compounds is described. Allylic alcohols and/or their acetates and allyl phenyl ethers were employed as allylating agents. The dependence of the reaction yield on nature and quantity of base and structure of the allylic unit is reported and explained. The lowest yield was obtained for allyl alcohol; however it could be considerably increased by addition of a stoichiometric amount of ethyl acetate. Order of reactivity of functions groups was OPh > OAc > OH. A novel method of synthesis of tetrakis (triphenylphosphine) palladium is also reported.