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

Ah ighly efficient synthesis of unsymmetrical sulfoximineu reas is developed. Ther eactionu nites simple NH-sulfoximines and acyl azides by af ormal Curtius rearrangementa st he key step. This reaction could be easily scaled up to gram scale and omits the generation of hazardous byproducts, thusa llowing ap ractical and environmentally benignp ath for the synthesis of medicinally important sulfonimidoyl unsymmetrical ureas.

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Highly Efficient Curtius Rearrangement Approach for the Synthesis of Unsymmetrical Sulfonimidoyl Ureas

Zhou

Hong

Huang

et al. 2017

Asian J Org Chem

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ChemInform Abstract: A Mild and Efficient Procedure for the N‐Functionalization of S‐Perfluoroalkylated Aryl Sulfoximines.

et al. 2013

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A Mild and Efficient Procedure for the N-Functionalization of S-Perfluoroalkylated Aryl Sulfoximines. -The title reaction is carried out with acid chlorides as reactants in the presence of base to give the corresponding functionalized amides. The method is extended to the synthesis of ureas, urethanes, thioureas, and C2-symmetrical bis-sulfoximes. -(MACE, Y.; CONSTANT-URBAN, C.; BOUVET, S.; PEGOT, B.; BOURNAUD, C.; TOFFANO, M.; VO-THANH, G.; DITER, P.; MAGNIER*, E.; Synthesis 45 (2013) 11, 1505-1512, http://dx.

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Fluorinated Sulfoximines: Preparation, Reactions and Applications

Shen

2014

Eur J Org Chem

133

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The selective incorporation of fluorine atoms or fluorinated moieties into organic molecules has become a “hot” research topic in modern organic chemistry. However, selective and efficient synthesis of organofluorine compounds greatly depends on the development of powerful fluorination or fluoroalkylation reagents and reactions. In this context, the past decade has witnessed rapid research progress in the development of α‐fluoro sulfoximines as versatile fluoroalkylation reagents. Many efficient nucleophilic, electrophilic and radical fluoroalkylation reactions based on α‐fluoro sulfoximine reagents have been developed; among these, several chiral sulfoximine reagents were successfully used in the synthesis of enantiomerically enriched organofluorine compounds. It was found that α‐fluoro sulfoximines show unique chemical behaviour characteristics (such as difluorocarbene and fluoroalkyl radical reactivities) significantly different from those of their non‐fluorinated counterparts. In addition to the rapid development of fluorinated sulfoximines in organic synthesis, research into their application in materials science has also attracted increasing attention. Sulfoximines are important bioactive substances, and more recently the synthesis and application of fluorinated sulfoximines has attracted much attention in life sciences and the pharmaceutical industry. In this microreview we summarize the preparation, reactions and applications of fluorinated sulfoximines (mainly α‐fluoro sulfoximines).

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

Cited by 8 publications

References 7 publications

Highly Efficient Curtius Rearrangement Approach for the Synthesis of Unsymmetrical Sulfonimidoyl Ureas

Highly Efficient Curtius Rearrangement Approach for the Synthesis of Unsymmetrical Sulfonimidoyl Ureas

ChemInform Abstract: A Mild and Efficient Procedure for the N‐Functionalization of S‐Perfluoroalkylated Aryl Sulfoximines.

Fluorinated Sulfoximines: Preparation, Reactions and Applications

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