Cycloadditions of CF3-Containing Alkynes

  • Author: ChemistryViews
  • Published: 04 February 2011
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
thumbnail image: Cycloadditions of CF<sub>3</sub>-Containing Alkynes

Benzene derivatives with trifluoromethyl groups have shown interesting biological activity, in part due to the presence of fluorine, a common motif in pharmaceuticals. Synthesis of substituted benzenes can be efficiently performed through [2 + 2+ 2] cycloadditions of alkynes, although examples with fluorine-containing alkynes are rare.

A ruthenium catalyst that catalyzes the [2 + 2 + 2] cycloaddition of fluorine-containing alkynes has now been reported by Motoi Kawatsura and colleagues, Tottori University, Japan. The catalyst consisted of Ru3(CO)12 coordinated with 2-(diphenylphosphino)benzonitrile. With this catalyst, CF3-substituted benzene derivatives could be made in up to 92 % yield with >98 % regioselectivity.

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