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2017 ; 23
(60
): 15189-15193
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A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of
Electrophilic NH to Sulfinamides
#MMPMID28833686
Izzo F
; Schäfer M
; Stockman R
; Lücking U
Chemistry
2017[Oct]; 23
(60
): 15189-15193
PMID28833686
show ga
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.