# Sulfoximine N‑Functionalization with N‑Fluorobenzenesulfonamide

## TL;DR

A new metal-free method for modifying sulfoximines using N-fluorobenzenesulfonamide is introduced, offering high yields and scalability.

## Contribution

A metal-free, scalable, and mild method for sulfoximine N-functionalization using N-fluorobenzenesulfonamide is developed.

## Key findings

- The method produces NH-sulfoximines in yields above 75% using EtOAc and TMP.
- The reaction supports various substrates like amines, hydrazides, phenols, and amino acids.
- Products were analyzed by NMR and X-ray crystallography and tested in further reactions.

## Abstract

An operationally simple, convenient, mild, metal-free,
and scalable
transformation of sulfoximines with N-fluorobenzenesulfonamide
is presented. A wide range of structurally different NH-sulfoximines were prepared and reacted with N-fluorobenzenesulfonamide
in the presence of TMP (2,2,6,6-Tetramethylpiperidine) and in the
environmentally friendly EtOAc to obtain the desired products, mostly
in yields above 75%. The method also supports various amine, hydrazide,
phenol, and amino acid substrates as well as scale-up to gram reactions
with minimal to no modification of the process. The products formed
from the sulfoximines were structurally analyzed by NMR and X-ray
crystallography and investigated for their stability and further reactivity
as substrates in Suzuki-Miyaura coupling, methylation, and bromination
reactions. In addition, DFT calculations were carried out with regard
to the energy profile and mechanism of the reaction.