Palladium Catalyzed Coupling of F-Vinyl Zinc Reagents with Aryl Iodides. An Improved Synthesis of Alpha, Beta, Beta-Trifluorostyrenes and the Stereospecific Preparation of 1-Phenyl-F-Propenes

摘要

Palladium catalyzed coupling of trifluorovinyl zinc reagents with substituted aryl iodides provides a practical high yield route to E, alpha, beta-trifluorostyrenes. Ortho, meta,and para substituted aryl iodides all work equally well. Simular coupling with E- and Z-1-iodo-F-propenes outlines the first sterospecific preparative route to 1-aryl-F-olefines. This approach provides a rapid, easily scaled-up synthesis via a one pot procedure to these valuable styrenes from commercially available precursors without recourse to low temperature processes or the use of unstable reaction intermediates.