[4‐(Acetylamino)phenyl]imidodisulfuryl Difluoride

Carneiro, Sabrina N.; Ball, Nicholas D.; Lee, Jisun; Ende, Christopher W. am

doi:10.1002/047084289x.rn02400

Encyclopedia of Reagents for Organic Synthesis 2021

DOI: 10.1002/047084289x.rn02400

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[4‐(Acetylamino)phenyl]imidodisulfuryl Difluoride

Sabrina N. Carneiro

Nicholas D. Ball

Jisun Lee

et al.

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2024

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“…18 Furthermore, in 2018, am Ende and co-workers developed [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF) as an alternative to SO 2 F 2 . 19,20 The design and application of AISF, which was utilized in the synthesis of fluorosulfates, attracted us to explore AISF as a carboxylic acid activator. AISF reacted with alcohols and amines to give fluorosulfates 19 and sulfamoyl fluoride.…”

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confidence: 99%

Synthesis of Amides and Peptides by Employing [4-(Acetylamino) phenyl]imidodisulfuryl Difluoride (AISF) as a Coupling Reagent

Bharamawadeyar,

Chetankumar,

Srinivasulu

et al. 2024

Synthesis

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A new synthetic approach for the preparation of amides and peptides containing amino acids as well as aryl acids and amines by employing [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF) as a carboxylic acid activator under mild conditions is delineated. The use of AISF as an acid activator allows the reaction to be performed efficiently. This operationally simple amidation is amenable to a wide variety of carboxylic acids and Nα-protected amino acids. Further, racemization did not occur during the coupling. In addition, a gram-scale reaction is demonstrated.

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confidence: 99%

Synthesis of Amides and Peptides by Employing [4-(Acetylamino) phenyl]imidodisulfuryl Difluoride (AISF) as a Coupling Reagent

Bharamawadeyar,

Chetankumar,

Srinivasulu

et al. 2024

Synthesis

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[4‐(Acetylamino)phenyl]imidodisulfuryl Difluoride

Cited by 1 publication

References 13 publications

Synthesis of Amides and Peptides by Employing [4-(Acetylamino) phenyl]imidodisulfuryl Difluoride (AISF) as a Coupling Reagent

Synthesis of Amides and Peptides by Employing [4-(Acetylamino) phenyl]imidodisulfuryl Difluoride (AISF) as a Coupling Reagent

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