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Synlett 2023; 34(14): 1723-1726
DOI: 10.1055/a-2043-4740
DOI: 10.1055/a-2043-4740
letter
Iodine/Sulfinates: Rapid and Convenient Thiolation of Imidazo Heterocycles without Additives
Authors
Financial support from Aix Marseille Université and the Centre National de la Recherche Scientifique (CNRS) is gratefully acknowledged.
Abstract
An unprecedented I2/sulfinate thiolating system is described for the sulfenylation of electron-rich heterocycles. This phosphine-free strategy permits simple, efficient, and fast sulfenylation of imidazo heterocycles, anilines, indoles, coumarins, or enaminones.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2043-4740.
- Supporting Information (PDF)
Publication History
Received: 02 January 2023
Accepted after revision: 27 February 2023
Accepted Manuscript online:
27 February 2023
Article published online:
29 March 2023
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- 10 Thio Ethers 3a–s: General Procedure The appropriate sodium sulfinate 2 (3 equiv) and I2 (1 equiv) were added to a solution of the heterocycle 1 (1 equiv) in DMF (1 mL) in a microwave vial. The vial was sealed and the mixture was heated at 120 °C by microwave irradiation for 2 h. The solution was then treated with sat. aq Na2S2O3 (10 mL) and the aqueous phase was extracted with EtOAc (3 × 15 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under a vacuum. 2-Phenyl-3-(phenylsulfanyl)imidazo[1,2-a]pyridine (3a) White solid; yield: 262 mg (87%); mp 110 °C. 1H NMR (400 MHz, CDCl3): δ = 8.27–8.29 (m, 1 H), 8.20–8.22 (m, 2 H), 7.75 (d, 1 H), 7.42–7.46 (m, 2 H), 7.33–7.40 (m, 2 H), 7.20–7.23 (m, 2 H), 7.12–7.16 (m, 1 H), 6.99–7.02 (m, 2 H), 6.86–6.90 (m, 1 H). 13C NMR (100 MHz, CDCl3): δ = 151.4, 147.2, 135.3, 133.3, 129.6 (2 CH), 128.8, 128.6 (2 CH), 128.5 (2 CH), 126.9, 126.2, 125.7 (2 CH), 124.7, 117.8, 113.3, 106.5, 106.7.