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7425365 
Journal Article 
Review 
Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy-amino-λ6 -sulfanenitrile Intermediate 
Briggs, EL; Tota, A; Colella, M; Degennaro, L; Luisi, R; Bull, JA; , 
2019 
Yes 
Angewandte Chemie (International Edition)
ISSN: 1433-7851
EISSN: 1521-3773 
Wiley-VCH Verlag 
58 
40 
14303-14310 
English 
31390133 
WOS:000483958000001 
Sulfonimidamides are intriguing new motifs for medicinal and agrochemistry, and provide attractive bioisosteres for sulfonamides. However, there remain few operationally simple methods for their preparation. Here, the synthesis of NH-sulfonimidamides is achieved directly from sulfenamides, themselves readily formed in one step from amines and disulfides. A highly chemoselective and one-pot NH and O transfer is developed, mediated by PhIO in iPrOH, using ammonium carbamate as the NH source, and in the presence of 1 equivalent of acetic acid. A wide range of functional groups are tolerated under the developed reaction conditions, which also enables the functionalization of the antidepressants desipramine and fluoxetine and the preparation of an aza analogue of the drug probenecid. The reaction is shown to proceed via different and concurrent mechanistic pathways, including the formation of novel S≡N sulfanenitrile species as intermediates. Several alkoxy-amino-λ6 -sulfanenitriles are prepared with different alcohols, and shown to be alkylating agents to a range of nucleophiles. 
hypervalent iodine; reactive intermediates; sulfonimidamides; sulfur; synthetic methods; Amides; Amines; Nucleophiles; Praseodymium compounds; Sulfur; Sulfur compounds; Ammonium carbamates; Functionalizations; Hypervalent iodine; Mechanistic pathways; Reaction conditions; Reactive intermediate; sulfonimidamides; Synthetic methods; Reaction intermediates; alcohol derivative; alkoxyl radical; amine; nitrile; sulfamerazine; sulfenamide; sulfonamide; chemical structure; chemistry; synthesis; Alcohols; Amines; Molecular Structure; Nitriles; Sulfamerazine; Sulfonamides 
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