TY - JOUR
T1 - Palladium-catalyzed decarboxylation-allylation of allylic esters of α-substituted β-keto carboxylic, malonic, cyanoacetic, and nitroacetic acids
AU - Tsuji, Jiro
AU - Yamada, Toshiro
AU - Minami, Ichiro
AU - Yuhara, Masami
AU - Nisar, Mohammad
AU - Shimizu, Isao
PY - 1987
Y1 - 1987
N2 - 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.
AB - 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.
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M3 - Article
AN - SCOPUS:0011446373
SN - 0022-3263
VL - 52
SP - 2988
EP - 2995
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 14
ER -