A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides

Izzo, Flavia; Sch�fer, Martina; Stockman, Robert; L�cking, Ulrich

Abstract

Unprotected tertiary sulfonimidamides have been prepared in good to excellent yields in a one‐pot transformation from tertiary sulfinamides through NH transfer. The reaction is mediated by commercially available (diacetoxyiodo)benzene and ammonium carbamate in methanol under convenient conditions. A wide range of functional groups are tolerated and initial results indicate that the NH transfer is stereospecific. A small molecule X‐ray analysis of NH sulfonimidamide 2 a and its behavior in selected in vitro assays in comparison to the matched sulfonamide are also reported. This new reaction provides a safe, short and efficient approach to sulfonimidamides, which have been the subject of recent, growing interest in the life sciences.

Citation

Izzo, F., Schäfer, M., Stockman, R., & Lücking, U. (2017). A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides. Chemistry - A European Journal, 23(60), 15189-15193. https://doi.org/10.1002/chem.201703272

• Journal Article Type: Article
• Acceptance Date: Aug 22, 2017
• Online Publication Date: Oct 9, 2017
• Publication Date: Oct 26, 2017
• Deposit Date: Apr 21, 2021
• Publicly Available Date: Apr 22, 2021
• Journal: Chemistry - A European Journal
• Print ISSN: 0947-6539
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 23
• Issue: 60
• Pages: 15189-15193
• DOI: https://doi.org/10.1002/chem.201703272
• Public URL: https://nottingham-repository.worktribe.com/output/1858643
• Publisher URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201703272