Chalcogenylation of Naphthalene Derivatives Catalyzed by Iron(III) Chloride and Potassium Iodide

Abstract

We have developed an efficient chalcogenylation of electron-rich naphthalene derivatives catalyzed by FeCl₃ and KI. The methodology provides access to several nonsymmetrical diorganoyl chalcogenides (S, Se) by selective C1 chalcogenylation of 2-naphthols or 2-naphthylamines using simple and cheap catalysts. Several control experiments supported the hypothesis that a redox reaction between Fe(III) and KI produces I₂, which catalyzed the chalcogenylation.

Key words

iron catalysis - potassium iodide catalysis - sulfanylation - selenylation - naphthylamines - naphthols

Publication History

Received: 21 December 2020

Accepted after revision: 05 March 2021

Article published online:
01 April 2021

• References and Notes

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• 21 Chalcogenylation of Naphthalene Derivatives Catalyzed by FeCl₃ and KI: General Procedure An oven-dried 10 mL glass tube was charged with the appropriate naphthalene derivative 1 (0.5 mmol, 1.0 equiv), diorganoyl dichalcogenide 2 or 4 (0.25 mmol), and KI (5.0 mol%, 4.1 mg). FeCl₃ (5.0 mol%, 4.0 mg) was then weighed quickly, dissolved in DMSO (2.0 mL), and added to the glass tube. The mixture was stirred at 110 °C for 24 h then cooled to r.t. and added to sat. aq Na₂S₂O₃ (5.0 mL). The resulting mixture was extracted with EtOAc (3 × 5.0 mL), and the organic extracts were separated, dried (MgSO₄), and concentrated under vacuum. The residue was purified by flash chromatography (silica gel, hexane–EtOAc) 1-(Phenylselanyl)-2-naphthol (3a)^6d Flash chromatography [silica gel, hexane–EtOAc (90:10)] gave a white solid; yield: 145.1 mg (97%); mp 77–78 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 10.21 (s, 1 H), 8.26 (dd, J = 8.5, 1.1 Hz, 1 H), 7.94 (d, J = 8.9 Hz, 1 H), 7.84 (dd, J = 8.1 and 1.3 Hz, 1 H), 7.46 (ddd, J = 8.4, 6.8, 1.4 Hz, 1 H), 7.36 (d, J = 8.9 Hz, 1 H), 7.32 (ddd, J = 8.0, 6.8, 1.2 Hz, 1 H), 7.16–7.09 (m, 5 H). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 158.1, 146.1, 136.5, 133.3, 132.5, 129.6, 129.1, 128.9, 128.0, 126.9, 126.0, 123.6, 118.6, 108.1. MS (EI): m/z (%) = 300 (32.2) [M⁺], 298 (16.1), 220 (100.0), 194 (29.9), 115 (80.8), 102 (13.1), 77 (18.9), 51 (30.8).