Synfacts 2008(8): 0862-0862  
DOI: 10.1055/s-2008-1078512
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Cross-Coupling of Potassium Alkoxymethyltrifluoroborates

Contributor(s): Paul Knochel, Andrei Gavryushin
G. A. Molander*, B. Canturk
University of Pennsylvania, Philadelphia, USA
Further Information

Publication History

Publication Date:
23 July 2008 (online)

Significance

Herein, a new efficient and robust method for the preparation of alkoxymethyltrifluoroborates starting from alkoxides and a common precursor, potassium bromomethyltrifluoroborate, is reported. The products can be cross-coupled with a broad variety of aryl and hetaryl chlorides, leading to O-substituted benzylic alcohols, or their heterocyclic analogues. Both reactions tolerate almost all functional groups. This method gives a direct and simple access to various benzylic esters.