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Synlett 2017; 28(13): 1558-1563
DOI: 10.1055/s-0036-1588728
DOI: 10.1055/s-0036-1588728
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Photoinduced Oxidative Cross-Coupling for O–S Bond Formation: A Facile Synthesis of Alkyl Benzenesulfonates
Further Information
Publication History
Received: 10 January 2017
Accepted after revision: 30 January 2017
Publication Date:
28 February 2017 (online)
Abstract
We have developed a photoinduced oxidative cross-coupling of thiophenols with alcohols for O–S bond formation. The protocol uses visible light, a metal-free photocatalyst, and oxygen as the oxidant for the selective synthesis of alkyl benzenesulfonates; no ligand co-additive is necessary. Mechanistic studies suggested that the disulfide and alkyl benzenesulfinate are involved as intermediates and that the transformation proceeds by a radical pathway.
Key words
photoredox catalysis - alkyl benzenesulfonates - C–S bond formation - dioxygen - oxidative coupling.Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588728.
- Supporting Information
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- 12 Alkyl Benzenesulfonates 3; General Procedure An oven-dried Schlenk tube equipped with a magnetic stirrer bar was charged with Acr+–Mes ClO4 – (5.0 mol%), capped with a septum, and evacuated. A balloon filled with O2 was connected to the Schlenk tube through the side arm, and thiophenol 1(1.0 mmol) and alcohol 2 (3.0 mL) were successively injected into the reaction tube. The mixture was irradiated with light from blue LEDs (3.0 W) and vigorously stirred at r.t. for 18–72 h (see Scheme 2). When the reaction was complete (TLC), the product was purified by flash column chromatography (silica gel, PE–EtOAc).