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Palladium‐Catalyzed Trifluoroethylation of Benzo[ h ]quinoline Derivatives by Mesityl(2,2,2‐trifluoroethyl)iodonium Triflate
Author(s) -
Han QiuYan,
Hu Xiaoxiao,
Xue XiaoSong,
Zhao ChengLong,
Zhang ChengPan
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900030
Subject(s) - chemistry , quinoline , trifluoromethanesulfonate , medicinal chemistry , palladium , catalysis , oxidative addition , stereochemistry , organic chemistry
Reactions of a dimeric [(bzq)Pd(OAc)] 2 complex ( 1 a′ ) and mesityl(2,2,2‐trifluoroethyl)iodonium triflate ( 2 a ) with or without additives at room temperature gave 10‐(2,2,2‐trifluoroethyl)benzo[ h ]quinoline rapidly in moderate to high yields. The reaction might proceed through a unstable binuclear “Pd III −CH 2 CF 3 ” intermediate ( I ), which was likely formed in situ from the oxidative addition of 2 a to [(bzq)Pd(OAc)] 2 and favorably transformed to mononuclear “(bzq)Pd IV −CH 2 CF 3 ” complexes ( III ) in the presence of another equiv.alent of 2 a and a suitable additive. Based on these, a Pd‐catalyzed C−H trifluoroethylation of benzo[ h ]quinolines with 2 a was developed. Numerous benzo[ h ]quinoline derivatives reacted with [MesICH 2 CF 3 ][OTf] at room temperature in the presence of 10 mol% Pd(OAc) 2 and 2 equiv.. NaHCO 3 to provide the corresponding 10‐trifluoroethylated products in excellent yields.