Copper‐Catalyzed S−C/S−N Bond Interconversions

Wen, Jianxun; Cheng, Hanchao; Dong, Shujuan; Bolm, Carsten

doi:10.1002/chem.201600661

Cited by 42 publications

(25 citation statements)

References 56 publications

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“…A number of methods for the synthesis of sulfonimidamides have been reported in the literature in the last five years. These approaches include: (i) reaction of sulfinamides with ammonium carbamate and PhI(OAc) 2 ; (ii) copper‐catalyzed oxidative S−C/S−N bond interconversion in the corresponding sulfones; (iii) sulfur(VI)–fluoride exchange (SufFEx) reactions in the corresponding sulfonimidoyl fluorides 1 (Figure ); (iv) nucleophilic substitution in unstable sulfonimidoyl chlorides 2 (Scheme ) . Many of these methods were either limited in scope or relied on the use of unstable and/or difficult‐to‐operate (e.g., gaseous or explosive) reagents.…”

Section: Introductionmentioning

confidence: 99%

Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space

Zasukha

Тимошенко

Tolmachev

et al. 2019

Chemistry A European J

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Two novel solid reagents—1‐sulfonimidoyl‐ and 1‐sulfamimidoyl‐3‐methylimidazolium derivatives—for the synthesis of sulfonimidamides and imidosulfuric diamides, respectively, were developed. It is shown that these reagents are very effective in substitution reactions with various N‐ and O‐nucleophiles; therefore, they significantly extend the accessibility to the chemical space covered by organosulfur(VI) compounds with S=N bonds. In addition, previously unknown imidosulfuric diamides with free imino nitrogen groups were prepared, and their physical and chemical properties were characterized (including molecular geometry, pKa, Log P, microsomal stability, and reactivity towards typical electrophiles). Similar to other organosulfur(VI) derivatives with S=N bonds, these compounds can be considered as promising bioisosteres of amides, ureas, or sulfonamides.

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Section: Introductionmentioning

confidence: 99%

Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space

Zasukha

Тимошенко

Tolmachev

et al. 2019

Chemistry A European J

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“…[7][8][9] Direct N À Ht ransfer to as ulfinamide has also been reported. [7][8][9] Direct N À Ht ransfer to as ulfinamide has also been reported.…”

Section: Sulfonamideshavearichhistoryinmedicinalchemistryandmentioning

confidence: 99%

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

2017

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Sulfonimidamides are increasingly important molecules in medicinal chemistry and agrochemistry, but their preparation requires lengthy synthetic sequences, which has likely limited their use. We describe a one-pot de novo synthesis of sulfonimidamides from widely available organometallic reagents and amines. This convenient and efficient process uses a stable sulfinylamine reagent, N-sulfinyltritylamine (TrNSO), available in one step on 10 gram scale, as a linchpin. In contrast to classical approaches starting from thiols or their derivatives, our TrNSO-based approach facilitates the rapid assembly of the three reaction components into a variety of differentially substituted sulfonimidamides containing medicinally relevant moieties, including pyridines and indoles. Analogues of the sulfonamide-containing COX-2 inhibitor Celecoxib were prepared and evaluated.

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“…[6] Sharpless and co-workers described the use of thionyl tetrafluoride (SOF 4 )a sauseful reagent for sulfur fluoride exchange (SuFEx) click chemistry,u sing sulfonimidoyl fluorides as precursors to sulfoximines,s ulfonimidates,a nd sulfonimid-amides. [12] Sulfonamides have also been converted into sulfonimidamides,w ith this approach being recently extended by Grygorenko and co-workers to form imidazolium salts as precursors to sulfonimidamides and imidosulfuric diamides. [12] Sulfonamides have also been converted into sulfonimidamides,w ith this approach being recently extended by Grygorenko and co-workers to form imidazolium salts as precursors to sulfonimidamides and imidosulfuric diamides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy‐amino‐λ⁶‐sulfanenitrile Intermediate

et al. 2019

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Sulfonimidamides are intriguing new motifs for medicinal and agrochemistry,a nd provide attractive bioisosteres for sulfonamides.However,there remain few operationally simple methods for their preparation. Here,t he synthesis of NH-sulfonimidamides is achieved directly from sulfenamides,themselves readily formed in one step from amines and disulfides.Ahighly 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 1equivalent of acetic acid. Awide range of functional groups are tolerated under the developed reaction conditions,w hich 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 SNsulfanenitrile species as intermediates.Several alkoxy-amino-l 6 -sulfanenitriles are prepared with different alcohols,a nd shown to be alkylating agents to arange of nucleophiles. Scheme 1. Potential bioisosteres for sulfones and sulfonamides, examples of bioactive sulfonimidamides, and current strategies for the synthesis of sulfonimidamides.

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Copper‐Catalyzed S−C/S−N Bond Interconversions

Cited by 42 publications

References 56 publications

Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space

Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy‐amino‐λ⁶‐sulfanenitrile Intermediate

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Copper‐Catalyzed S−C/S−N Bond Interconversions

Cited by 42 publications

References 56 publications

Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space

Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy‐amino‐λ6‐sulfanenitrile Intermediate

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Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy‐amino‐λ⁶‐sulfanenitrile Intermediate