Synthesis of 3‐CF3‐Indoles from HFO‐1234ze(E) via Cross‐Coupling and Intramolecular Cyclization

The synthesis of indoles with a trifluoromethyl group has attracted a lot of attention because they are promising structural subunits for pharmaceuticals and agrochemicals. As part of our project aimed toward the upcycling of hydrofluoroolefins (HFOs), we developed a method to construct a CF3‐bearin...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-08, Vol.366 (16), p.3455-3459
Main Authors: Mizuno, Shota, Yotsume, Futa, Kasahara, Runa, Inoue, Munenori, Ichikawa, Junji, Fujita, Takeshi
Format: Article
Language:English
Subjects:
5-endo-trig Cyclization
Agrochemicals
Bromination
Cross coupling
C−F Bond activation
Hydrofluoroolefins (HFOs)
Indoles
Synthesis
Toluene
Upcycling
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Summary:The synthesis of indoles with a trifluoromethyl group has attracted a lot of attention because they are promising structural subunits for pharmaceuticals and agrochemicals. As part of our project aimed toward the upcycling of hydrofluoroolefins (HFOs), we developed a method to construct a CF3‐bearing indole ring system through the Suzuki–Miyaura cross‐coupling of a brominated HFO‐1234ze(E) (CF3CH=CHF) with N‐tosylated o‐borylanilines, followed by nucleophilic 5‐endo‐trig cyclization at the vinylic position of the generated fluorostyrenes. We found that the Pd2(dba)3/SPhos catalyst system in the presence of K2CO3 and water in toluene afforded the corresponding 3‐CF3‐indoles in high yields in a one‐pot operation.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400508