Hydrogenation of fluoroarenes: Direct access to all- cis -(multi)fluorinated cycloalkanes

Abstract

Keeping all fluorines on the same side Carbon-fluorine bonds are highly polarized, and this effect is magnified when several of them reside on the same face of a saturated ring. However, most existing fluorination methods have difficulty consistently producing this all-cis mutual configuration. Wiesenfeldt et al. used a rhodium catalyst in nonpolar solvent to add hydrogens selectively to just one face of a wide variety of flat fluoroarene rings, pushing all fluorines toward the other face. The reaction also pushed fluorine toward the same face as nitrogen and oxygen in heterocycles such as indole and benzofuran. Science , this issue p. 908