Synthesis of Diaryl Diselenides and Ditellurides via Bromide-Catalyzed C–Se/C–Te Bond Formation Using Se/Te Powder and Boronic Acid

Abstract

Diaryl diselenides and diaryl ditellurides are commonly employed as selenyl or telluryl sources, and they have a wide range of applications in organic synthesis. Herein, various diaryl diselenides/ditellurides are furnished in moderate to excellent yields under metal-free conditions. This method features high efficiency, good functional group tolerance, straightforward operation, and easy scale-up (running in 4 mmol-scale for most cases). Mechanistic studies indicate that this reaction may proceed via a radical pathway. Significantly, the correct matching of Br^– and dimethyl sulfoxide under an air atmosphere is critical to this transformation.

Key words

diselenides - bromide-catalysis - Se powder - boronic acid - radical pathway

Publication History

Received: 26 July 2024

Accepted after revision: 23 September 2024

Accepted Manuscript online:
23 September 2024

Article published online:
09 October 2024

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• 9 Synthesis of Diphenyl Diselenide (2a); Typical Procedure: Under air atmosphere, a mixture of boronic acid 1 (4 mmol, 1 equiv), Se (4.8 mmol, 1.2 equiv), NH₄Br (0.8 mmol, 0.2 equiv), and DMSO (8 mL) was added to a 25 mL round-bottom flask. The obtained solution was stirred at 120 °C for 12 hours. When the reaction was complete, the reaction was quenched with H₂O (10 mL) and the mixture was extracted with EtOAc (3 × 15 mL). The combined organic phase was dried with anhydrous Na₂SO₄ and filtered. The filtrate was concentrated under reduced pressure to give a crude residue, which was purified by flash column chromatography to provide the desired product 2a (508.7 mg, 81% yield) as a yellow solid. ¹H NMR (500 MHz, CDCl₃): δ = 7.61–7.56 (m, 4 H), 7.26–7.19 (m, 6 H). The NMR spectra were identical to those previously reported in ref. 5a.