Decarboxylation-allylation of allylic β-keto carboxylates using Pd(OAc)2-PPh3 or Pd2(dba)3·CHCl3-dppe as a catalyst proceeds smoothly to give α-allylated ketones. The reaction is highly regioselective. In some cases, diallylated ketones are obtained with allylic esters bearing an active proton(s). Also rhodium, molybdenum, and nickel complexes are active catalysts in this reaction. Similarly allylic esters of α-substituted malonates, cyanoacetates, and nitroacetate undergo the palladium-catalyzed decarboxylation-allylation to afford allylated acetate, acetonitrile, and nitromethane, respectively. The mechanisms of these palladium-catalyzed decarboxylation-allylations are discussed.
|Number of pages||8|
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 1987|
ASJC Scopus subject areas
- Organic Chemistry