Synthesis of Symmetrical Disulfides by an NIS/PPh₃-Mediated Reductive Self-Coupling of Sulfonyl Hydrazides

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

disulfides - arylsulfonyl hydrazides - aryl disulfides - reductive coupling

Publication History

Received: 21 August 2023

Accepted after revision: 10 October 2023

Article published online:
10 November 2023

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• 14 1,2-Di-p-tolyl Disulfide (2a); Typical Procedure of Synthesis: A 50 mL round-bottomed flask equipped with a magnetic stirring bar was charged with 1a (50 mg, 0.268 mmol), NIS (150.0 mg, 0.670 mmol), and PPh₃ (210.0, 0.804 mmol) in CH₃CN (2 mL). 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.