A Mild and Efficient Procedure for the N-Functionalization of S-Perfluoroalkylated Aryl Sulfoximines

Yohan Macé; Céline Constant-Urban; Sébastien Bouvet; Bruce Pégot; Chloée Bournaud; Martial Toffano; Giang Vo-Thanh; Patrick Diter; Emmanuel Magnier

doi:10.1055/s-0033-1338440

Synthesis, Table of Contents

Synthesis 2013; 45(11): 1505-1512
DOI: 10.1055/s-0033-1338440

paper

A Mild and Efficient Procedure for the N-Functionalization of S-Perfluoroalkylated Aryl Sulfoximines

Authors

Yohan Macé

^aInstitut Lavoisier de Versailles (ILV), UMR CNRS 8180, Université de Versailles, St Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France Email: emmanuel.magnier@uvsq.fr

^bLaboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR CNRS 8182, Université Paris-Sud 11, 91405 Orsay Cedex, France Email: giang.vo-thanh@u-psud.fr
Céline Constant-Urban

^aInstitut Lavoisier de Versailles (ILV), UMR CNRS 8180, Université de Versailles, St Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France Email: emmanuel.magnier@uvsq.fr
Sébastien Bouvet

^aInstitut Lavoisier de Versailles (ILV), UMR CNRS 8180, Université de Versailles, St Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France Email: emmanuel.magnier@uvsq.fr
Bruce Pégot

^aInstitut Lavoisier de Versailles (ILV), UMR CNRS 8180, Université de Versailles, St Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France Email: emmanuel.magnier@uvsq.fr
Chloée Bournaud

^bLaboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR CNRS 8182, Université Paris-Sud 11, 91405 Orsay Cedex, France Email: giang.vo-thanh@u-psud.fr
Martial Toffano

^bLaboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR CNRS 8182, Université Paris-Sud 11, 91405 Orsay Cedex, France Email: giang.vo-thanh@u-psud.fr
Giang Vo-Thanh*

^bLaboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), UMR CNRS 8182, Université Paris-Sud 11, 91405 Orsay Cedex, France Email: giang.vo-thanh@u-psud.fr
Patrick Diter

^aInstitut Lavoisier de Versailles (ILV), UMR CNRS 8180, Université de Versailles, St Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France Email: emmanuel.magnier@uvsq.fr
Emmanuel Magnier*

^aInstitut Lavoisier de Versailles (ILV), UMR CNRS 8180, Université de Versailles, St Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France Email: emmanuel.magnier@uvsq.fr

Abstract

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Abstract

N-Acylated perfluoroalkylated sulfoximines are synthesized easily from the corresponding free NH-sulfoximines on reaction with acid chlorides. This mild procedure is extended to diacid chlorides for the preparation of dimeric N-bridged sulfoximines and to reactions with chloroformates, carbamoyl chlorides, chlorothionoformates and thiocarbamoyl chlorides as electrophiles.

Key words

fluorinated sulfoximines - acylation - carbamoylation - ureas - N-bridged sulfoximines

Full Text

References

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Supplementary Material

Supporting Information (PDF) (opens in new window)