Cascade Radical Trifluoromethylthiolation/Cyclization of Dienes To Access SCF3-Containing Medium-Sized Heterocycles. 2023

Zhen Zhang, and Xiangshan Fang, and Ayimnisa Aili, and Shilong Wang, and Junhong Tang, and Wanjun Lin, and Lei Xie, and Jinchun Chen, and Kai Sun
College of Chemistry and Chemical Engineering, Yantai University, Yantai, 264005, P. R. China.

A novel radical cascade trifluoromethylthiolation/cyclization of dienes (N-alkyl-2-(1-phenylvinyl)aniline derivatives) with AgSCF3 has been developed. This approach provides simple and efficient access to a wide range of SCF3-containing medium-sized rings (7/8/9-membered heterocycles). Preliminary mechanistic studies suggest that the reaction is realized through a silver-assisted radical cascade cyclization process. The large-scale experiment and modification of the product reveal the promising utility of this protocol.

UI MeSH Term Description Entries
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D006571 Heterocyclic Compounds Cyclic compounds that include atoms other than carbon in their ring structure. Heterocyclic Compound,Compound, Heterocyclic,Compounds, Heterocyclic
D000475 Alkenes Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408) Alkene,Olefin,Olefins,Pentene,Pentenes
D000814 Aniline Compounds Compounds that include the aminobenzene structure. Phenylamine,Phenylamines,Anilines,Compounds, Aniline

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