Direct and Chemoselective Electrophilic Monofluoromethylation of Heteroatoms (-, , -, -, -) with Fluoroiodomethane.

The commercially available fluoroiodomethane represents a valuable and effective electrophilic source for transferring the CHF unit to a series of heteroatom-centered nucleophiles under mild basic conditions. The excellent manipulability offered by its liquid physical state (bp 53.4 °C) enables practical and straightforward one-step nucleophilic substitutions to retain the chiral information embodied, thus allowing it to overcome the requirement for fluoromethylating agents with no immediate access. The high-yielding methodology was successfully applied to a variety of nucleophiles including a series of drugs currently in the market.