32013-47-1Relevant articles and documents
Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides
Kanyiva, Kyalo Stephen,Shibata, Takanori,Uchida, Kanako
, p. 1377 - 1384 (2021/06/06)
We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a sulfonyl radical, and coupling of sulfonyl radical with a benzyl radical formed via hydrogen abstraction by sulfate anion radical. The practicality of the present reaction is demonstrated by a gram-scale synthesis and one-step synthesis of anticancer-active compound. The mechanism studies are conducted using radical scavengers and deuterated toluene.
Diverse structural assemblies of U-shaped hydrazinyl-sulfonamides: experimental and theoretical analysis of non-covalent interactions stabilizing solid state conformations
Andleeb, Hina,Khan, Imtiaz,Franconetti, Antonio,Tahir, Muhammad Nawaz,Simpson, Jim,Hameed, Shahid,Frontera, Antonio
, p. 1780 - 1793 (2019/03/19)
The present study describes the synthesis of five new hydrazinyl-sulfonamide derivatives incorporating linear and branched alkyl chains. An efficient and straightforward synthetic approach was used to achieve these sulfonamide compounds in good yields. Th
α-Amino Acid Sulfonamides as Versatile Sulfonylation Reagents: Silver-Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization
Kanyiva, Kyalo Stephen,Hamada, Daisuke,Makino, Sohei,Takano, Hideaki,Shibata, Takanori
supporting information, p. 5905 - 5909 (2018/09/14)
We developed a silver-catalyzed strategy for the generation of sulfonyl radicals from sulfonamides derived from α-amino acids. The reaction proceeded via a decarboxylation, N–S bond cleavage and radical cyclization sequence and allows the difunctionalization of alkynes and the synthesis of 3-sulfonylated coumarins. The reaction tolerated a broad scope of substrates and functional groups and could be extended to the synthesis of oxindoles and an isoquinolinedione by the capturing of the sulfonyl radical with an alkene moiety. Moreover, the proposed mechanism was supported experimentally and by DFT calculations.
