Bulletin of the Chemical Society of Japan p. 3531 - 3538 (1988)
Update date:2022-08-10
Topics:
Akiyama, Takeo
Kato, Kohji
Kajitani, Masatsugu
Sakaguchi, Yoshio
Nakamura, Junko
et al.
The photochemical introduction of trifluoromethyl group with CF3Br in aromatic and heteroaromatic rings was investigated for 9 compounds.Naphthalene, anthracene, anisole, N,N-dimethylaniline, ferrocene, benzothiophene, isoquinoline, and N-methylpyrrole gave trifluoromethylated products in 6.5-100percent yields.In one step from uracil, a pharmacologically important 5-trifluoromethyluracil can be synthesized by this method in 11percent yield.Based on the mechanistic study carried out for the naphthalene-CF3Br-CH3CN system, the reaction is found to proceed via the electron transfer from an excited singlet state of naphthalene to CF3Br.
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