Photochemical Trifluoromethylation of Some Aromatic and Heteroaromatic Compounds with Trifluoromethyl Bromide

Autor:	Junko Nakamura, Yoshio Sakaguchi, Kohji Kato, Masatsugu Kajitani, Hisaharu Hayashi, Takeo Akiyama, Akira Sugimori
Rok vydání:	1988
Předmět:	chemistry.chemical_compound Anthracene Trifluoromethyl chemistry Ferrocene Trifluoromethylation Thiophene Organic chemistry General Chemistry Isoquinoline Anisole Photochemistry Naphthalene
Zdroj:	Bulletin of the Chemical Society of Japan. 61:3531-3537
ISSN:	1348-0634 0009-2673
Popis:	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, benzo[b]thiophene, isoquinoline, and N-methylpyrrole gave trifluoromethylated products in 6.5–100% yields. In one step from uracil, a pharmacologically important 5-trifluoromethyluracil can be synthesized by this method in 11% 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8afc1bcdbcb02a1f4de49e6a36c9a831 https://doi.org/10.1246/bcsj.61.3531 Zobrazit plný text záznamu