Jump to main content
Jump to site search

Issue 32, 2014
Previous Article Next Article

Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides

Author affiliations

Abstract

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.

Graphical abstract: Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 May 2014, accepted on 26 Jun 2014 and first published on 26 Jun 2014


Article type: Paper
DOI: 10.1039/C4OB01088D
Citation: Org. Biomol. Chem., 2014,12, 6190-6199
  •   Request permissions

    Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides

    D. E. Stephens, G. Chavez, M. Valdes, M. Dovalina, H. D. Arman and O. V. Larionov, Org. Biomol. Chem., 2014, 12, 6190
    DOI: 10.1039/C4OB01088D

Search articles by author

Spotlight

Advertisements