Synfacts 2007(12): 1300-1300  
DOI: 10.1055/s-2007-991319
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Reductive Perfluoroalkylation of Esters with Perfluoroalkyl Titanates

Contributor(s): Paul Knochel, Andrei Gavryushin
K. Mikami*, T. Murase, Y. Itoh
Tokyo Institute of Technology, Japan
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22. November 2007 (online)


This method represents an easy way for the preparation of secondary alcohols, bearing a perfluorinated chain. The reaction of a perfluoroalkylmagnesium species with Ti(Oi-Pr)4 gives an at room temperature remarkably stable perfluoroalkylmetallic reagent, which easily reacts with aldehydes and esters. In both cases, the product is a perfluorinated secondary alcohol. The discovery of a stable perfluoroalkyl metal species should lead to other useful synthetic methods in this interesting field of organic synthesis.