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

University of British Columbia

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]

Text

2015-04-28

Attribution-NonCommercial-NoDerivs 2.5 Canada

http://hdl.handle.net/2429/52974

Chemistry

University of British Columbia

UBCV

http://creativecommons.org/licenses/by-nc-nd/2.5/ca/