Monofluoromethylation of Cyclic Sulfamidates and Sulfates with α‐Fluorocarbanions of Fluorobis(phenylsulfonyl)methane and Ethyl 2‐Fluoroacetoacetate

Abstract

A regioselective fluoromethylation by ring‐opening of cyclic sulfamidates and sulfates with α‐fluorocarbanions and subsequent reductive desulfonylation is developed. Fluorobis(phenylsulfonyl)methane (FBSM) was explored as fluoromethide equivalent and the reaction was extended to the α‐fluorocarbanion of ethyl 2‐fluoroacetoacetate. This approach allows access to γ‐ and δ‐fluoroamines as well as γ‐ and δ‐fluoroalcohols in high yields.