Heterogeneous Photocatalytic Radical Synthesis of Aryl Allyl Sulfones

Abstract

A photocatalytic synthesis of aryl allyl sulfones by a radical cascade reaction from an aryl diazonium salt, DABCO·(SO₂)₂ and 3-bromoprop-1-ene has been developed. This reaction employed ­DABCO·(SO₂)₂ as the SO₂ source and a polyaniline–graphitic carbon ­nitride–titanium dioxide composite as the photocatalyst. A series of substrates were tolerated, providing the corresponding products in good yields. Moreover, the photocatalyst could be readily recovered and reused several times with only a slight decrease in its catalytic activity.

Key words

photocatalysis - heterogeneous catalysis - semiconductor catalyst - radical cascade reaction - aryl allyl sulfones

Publication History

Received: 28 July 2022

Accepted after revision: 06 September 2022

Article published online:
14 October 2022

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• 13 1-(Allylsulfonyl)-4-nitrobenzene (2a): Typical ProcedureA 25 mL flask equipped with a stirrer bar was charged with 4-nitrobenzenediazonium tetrafluoroborate (1a; 0.75 mmol, 1.5 equiv), DABCO (1 mmol, 2 equiv), 3-bromoprop-1-ene (0.5 mmol, 1 equiv), and PANI(40%)–g-C₃N₄–TiO₂ (20 mg) in MeCN (5 mL). The mixture was then irradiated with a 30 W CFL (10 cm distance) and stirred at rt under N₂ for 10 h. When the reaction was complete, the catalyst was collected by filtration and the mixture was extracted with EtOAc. The organic layer was dried (Na₂SO₄) and concentrated in vacuum, and the residue was purified by flash column chromatography (silica gel PE–EtOAc) to give a yellow solid; yield: 91.9 mg (81%).¹H NMR (400 MHz, CDCl₃): δ = 8.40 (d, J = 8.9 Hz, 2 H), 8.07 (d, J = 8.9 Hz, 2 H), 5.80 (ddt, J = 17.5, 10.1, 7.4 Hz, 1 H), 5.37 (dd, J = 10.2, 0.7 Hz, 1 H), 5.15 (dd, J = 17.1, 1.0 Hz, 1 H), 3.87 (d, J = 7.4 Hz, 2 H). ¹³C NMR (100 MHz, CDCl₃) δ = 150.9, 143.7, 130.1, 125.6, 124.2, 123.9, 60.7. MS (ESI): m/z = 228.2 [M + H]⁺.