N-Fluorobenzenesulfonimide

Introduction

N-Fluorobenzenesulfonimide (NFSI) is a colorless crystalline powder with a melting point of 114–116 °C. One of the most convenient routes to prepare NFSI in high yield is the fluorination with 10% v/v F₂ in N₂ of N-(phenyl­sulfonyl)benzenesulfonamide in MeCN at –40 °C (Scheme [1]).[ ¹ ] NFSI can also be prepared from the corresponding sodium salt.[ ² ] NFSI has been widely used as an electrophilic fluorinating agent most particularly in the field of asymmetric electrophilic fluorination.[ ³ ] But NFSI is more than an electrophilic fluorinating agent: It is also a strong oxidant for organometallic intermediates to promote reductive elimination through high-oxidation-state transition metals, an amination reagent and even a phenylsulfonyl group transfer reagent.

Scheme 1 Synthesis of N-fluorobenzenesulfonimide (NFSI)

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