Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides.
David E Stephens, Gabriel Chavez, Martin Valdes, Monica Dovalina, Hadi D Arman, Oleg V Larionov
文献索引：Org. Biomol. Chem. 12(32) , 6190-9, (2014)
全文：HTML全文
摘要
The scope and mechanistic implications of the direct transformation of heterocyclic N-oxides to 2-trifluoromethyl-, and related perfluoroalkyl- and perfluoroaryl-substituted N-heterocycles has been studied. The reaction is effected by perfluoroalkyl- and perfluorophenyltrimethylsilane in the presence of strong base. In situ displacement of the para-fluoro substituent in the pentafluorophenyl ring and the methoxy group in 8-methoxyquinolines with additional nucleophiles allows for further site-selective refunctionalization of the N-heterocyclic products.
相关化合物
相关文献：
A Facile New Method for the Two-step Substitution of Hydroxy Groups in Primary Alcohols for Trifluoromethyl and Pentafluoroethyl Moieties. Sevenard DV, et al.
[Synlett 2001(03) , 0379-0381, (2001)]
Experimental determination of the conformational free energies (A values) of fluorinated substituents in cyclohexane by dynamic 19 F NMR spectroscopy. Part 2. Extension to fluoromethyl, difluoromethyl, pentafluoroethyl, trifluoromethylthio and trifluoromethoxy groups. Carcenac Y, et al.
[New J. Chem. 30(3) , 447-457, (2006)]