Formation of quaternary carbon center with a trifluoromethyl group using a Pd-catalyzed allylation reaction.
Synthesis of compounds with quaternary carbons is one of the most attractive reactions in the synthetic chemistry. However, there are only a few reports on synthesis of the compounds with a fluoroalkyl group at a quaternary carbon center. Recently, we reported the synthesis of alpha-trifluoromethylated ketones by the reaction of alpha,beta-unsaturated ketones with CF(3)-I using a Rh catalyst. When the alpha-trifluoromethylated ketones and allyl carbonates were treated with a Pd catalyst, the allylation reaction proceeded smoothly at the trifluoromethylated carbon to give the desired compounds with a trifluoromethylated quaternary carbon center in good to excellent yields.
Sato
Kazuyuki
K
Faculty of Pharmaceutical Sciences, Setsunan University, Hirakata, Osaka 573-0101, Japan.
Takiguchi
Yu
Y
Yoshizawa
Yosuke
Y
Iwase
Kayoko
K
Shimizu
Yoshie
Y
Tarui
Atsushi
A
Omote
Masaaki
M
Kumadaki
Itsumaro
I
Ando
Akira
A
D000498:Allyl Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D005617:Chlorofluorocarbons, Methane / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis*; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry*
D000498:Allyl Compounds; D005617:Chlorofluorocarbons, Methane; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D010165:Palladium; D002244:Carbon; C009554:fluoroform