2016
DOI: 10.1002/ange.201602320
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Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides

Abstract: An ew system for NH transfer is developed for the preparation of sulfoximines,w hicha re emerging as valuable motifs for drug discovery.T he protocol employs readily available sources of nitrogen without the requirement for either preactivation or for metal catalysts.M ixing ammonium salts with diacetoxyiodobenzene directly converts sulfoxides into sulfoximines.T his report describes the first example of using of ammonia sources with diacetoxyiodobenzene to generate an electrophilic nitrogen center.C ontrol an… Show more

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Cited by 61 publications
(49 citation statements)
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“…Our attention was captured by ar ecent report from Luisi, Bull and co-workerso utlining the use of am ixture of ammonium carbamate and (diacetoxyiodo)benzene [PhI(OAc) 2 ]f or the direct conversion of sulfoxides 8 into NH sulfoximines 4 at room temperature (Scheme 3). [20] Furthermore, this facile and new NHtransfer methodw as applicable to aw ide substrate scope and tolerated al arge number of heterocyclesa nd otherf unctionalities. [21] Attracted by the use of commercial reagents and the robust results of this new one-pot method,w ew erei ntrigued as to whether these safe reactionc onditions could also be usefulf or the facile synthesis of sulfonimidamides 2 by NH transfer to sulfinamides 6.…”
Section: Introductionmentioning
confidence: 97%
“…Our attention was captured by ar ecent report from Luisi, Bull and co-workerso utlining the use of am ixture of ammonium carbamate and (diacetoxyiodo)benzene [PhI(OAc) 2 ]f or the direct conversion of sulfoxides 8 into NH sulfoximines 4 at room temperature (Scheme 3). [20] Furthermore, this facile and new NHtransfer methodw as applicable to aw ide substrate scope and tolerated al arge number of heterocyclesa nd otherf unctionalities. [21] Attracted by the use of commercial reagents and the robust results of this new one-pot method,w ew erei ntrigued as to whether these safe reactionc onditions could also be usefulf or the facile synthesis of sulfonimidamides 2 by NH transfer to sulfinamides 6.…”
Section: Introductionmentioning
confidence: 97%
“…[19,20] As am odel substrate for optimization, sulfenamide 1a was prepared from Ph 2 S 2 and piperidine in the presence of silver nitrate (Table 1), using ap rocedure modified from that developed by Davis. [14] Pleasingly,t he expected sulfonimidamide 2a was observed as the main product. [14] Pleasingly,t he expected sulfonimidamide 2a was observed as the main product.…”
Section: Resultsmentioning
confidence: 92%
“…Thei nfluence of sodium acetate on the reaction in tBuOH (Scheme 5), and the inability of NaOAc to break down the sulfanenitrile (Scheme 6), suggested an additional role for acetate in the reaction mechanism. [14] Theiodonitrene rapidly reacts with the sulfenamide to form as ulfinamidine salt. When using tetrabutylammonium acetate essentially the same product distribution was seen, indicating that there is no effect from the sodium counterion on the l 6 -sulfanenitrile (entry 2).…”
Section: Forschungsartikelmentioning
confidence: 99%
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“…[13] In 2016, we reported af acile metal-free protocol for the direct synthesis of NH-sulfoximines from sulfoxides in high yields and with good functional group compatibility. [14] The NH transfer occurred with sources of ammonia, with ammonium carbamate preferred, in the presence of bis-(acetoxy)iodobenzene as the oxidant. Our approach has been recently extended by Stockman and Lücking to form sulfonimidamides,u sing closely related conditions to effect NH transfer to sulfinamides (Scheme 1c).…”
Section: Introductionmentioning
confidence: 99%