P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones

The synthesis, structure and reactivity of the fluoroaryl phosphinic acid HF4C6–P(O)HOH is reported and compared to a sterically comparable yet non-fluorinated analog with similar size. The fluoroaryl phosphinic acid undergoes reversible P–H addition to the carbonyl functionality of ketones under formation of a P–C bond which is retained in the resulting α-hydroxy phosphinic acid. The latter shows an extended 2D hydrogen bonded network in the solid state.