期刊
ACS CATALYSIS
卷 8, 期 3, 页码 2173-2180出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03220
关键词
C-H activation; trifluoroethylation; indoles; palladacycle; Catellani reaction
资金
- National Nature Science Foundation of China [21532009, 21472219, 21761142010, 21790330]
- National Basic Research Program of China [973-2015CB856600]
- Program of Shanghai Academic/Technology Research Leader [17XD1404500, 17JC1401200]
- strategic Priority Research Program [XDB20000000]
- Key Research Program of Frontier Science of the Chinese Academy of Sciences [QYZDJSSW-SLH055]
- Key Laboratory of Functional Molecular Engineering of Guangdong Province (South China University of Technology) [2016kf02]
A selective palladium-catalyzed trifluoroethylation reaction of indoles has been developed. The C-H bond activation process, using CF3CH2I as the fluoroalkyl source, can be employed to prepare a variety of 2-CF3CH2 substituted indoles. Moreover, because it displays a wide functional group tolerance, the process can be employed to synthesize CF3CH2-containing bioactive indoles through late-stage trifluoroethylation. The results of a preliminary mechanistic study and DFT calculations show that a beta-diketone, acting as an ionic palladium ligand, plays an important role in governing the efficiency of the palladium-catalyzed trifluoroethylation reaction by accelerating the oxidative addition step. In contrast, transfer of the indole N-H proton in the palladium center is involved in the rate-determining step.
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