Synlett, Table of Contents Synlett 2024; 35(12): 1453-1457DOI: 10.1055/s-0041-1738457 letter Synthesis of Symmetrical Disulfides by an NIS/PPh3-Mediated Reductive Self-Coupling of Sulfonyl Hydrazides Authors Ashvani Yadav Amrit Gond Virendra Prasad∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract The present study discloses an NIS/PPh3-mediated reductive self-coupling of arylsulfonyl hydrazides to prepare symmetric diaryl disulfides. This methodology has a broad functional-group tolerance and a high scalability. This strategy permits the introduction of sulfonyl hydrazides into the synthesis of symmetrical organic disulfides without the use of a catalyst or base, and symmetrical aromatic disulfides can be prepared in moderate to excellent isolated yields from inexpensive and readily available starting materials. Key words Key wordsdisulfides - arylsulfonyl hydrazides - aryl disulfides - reductive coupling Full Text References References and Notes 1a Gardiner DM, Waring P, Howlett BJ. Microbiology 2005; 151: 1021 1b Welch TR, Williams RM. Nat. Prod. Rep. 2014; 31: 1376 1c Li G.-Y, Li B.-G, Yang T, Yan J.-F, Liu G.-Y, Zhang G.-L. J. Nat. Prod. 2006; 69: 1374 1d Sun Y, Takada K, Takemoto Y, Yoshida M, Nogi Y, Okada S, Matsunaga S. J. Nat. Prod. 2012; 75: 111 1e Scharf D, Habel A, Heinekamp T, Brakhage A, Hertweck C. J. Am. Chem. Soc. 2014; 136: 11674 1f Chankhamjon P, Boettger-Schmidt D, Scherlach K, Urbansky B, Lackner G, Kalb D, Dahse H.-M, Hoffmeister D, Hertweck C. Angew. Chem. Int. Ed. 2014; 53: 13409 1g Kondo T, Mitsudo T.-a. Chem. Rev. 2000; 100: 3205 1h Taniguchi N. J. Org. Chem. 2007; 72: 1241 1i Talla A, Driessen B, Straathof NJ. W, Milroy L.-G, Brunsveld L, Hessel V, Noël T. Adv. Synth. Catal. 2015; 357: 2180 1j Zhang L, Chou CP, Moo-Young M. Biotechnol. 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The flask was placed in a preheated oil bath at 80 °C, and the mixture stirred under reflux for 8 h, then cooled to r.t. The CH3CN was evaporated under reduced pressure, then the crude mixture was diluted with EtOAc and extracted with sat. aq Na2S2O3. The resulting organic solution was dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography [silica gel, EtOAc–hexane (1:9)] to give a white solid; yield: 62.7 mg (95%, 0.252 mmol); mp 43–45 °C. 1H NMR (500 MHz, CDCl3): δ = 7.39 (d, J = 8.0 Hz, 4 H), 7.12 (d, J = 8.0 Hz, 4 H), 2.33 (s, 6 H). 13C NMR (125 MHz, CDCl3): δ = 137.5, 134.0, 129.8, 128.6, 21.1. Supplementary Material Supplementary Material Supporting Information (PDF)
