Ni-catalyzed ortho-directed trifluoromethylthiolation of aryl chlorides and bromides

This thesis describes a novel method to generate trifluoromethanesulfenyl arene or heteroarene products via Ni-catalyzed ortho-selective C-X (X = Cl or Br) activation. Successful C-X activation requires directing groups, but it is highly selective and allows aryl chlorides to be used and shows an ap...

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Bibliographic Details
Main Author: Nguyen, Tin
Language:English
Published: University of British Columbia 2015
Online Access:http://hdl.handle.net/2429/52974
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Summary:This thesis describes a novel method to generate trifluoromethanesulfenyl arene or heteroarene products via Ni-catalyzed ortho-selective C-X (X = Cl or Br) activation. Successful C-X activation requires directing groups, but it is highly selective and allows aryl chlorides to be used and shows an appreciable substrate scope. The protocol tolerates various nitrogen-containing directing groups including imines, pyridines, pyrimidines, amides and oxazolines. The method is also compatible with aryl halides bearing substituents with a wide rage of electronic properties, including electron-donating or withdrawing abilities, as well as potentially sensitive functional groups. It also produces trifluoromethylthiolated arenes in good-to-excellent yields at ambient temperatures. [formula omitted] === Science, Faculty of === Chemistry, Department of === Graduate