Sulfoximines as S-Aryl Surrogates: A Photocatalytic Rapid, Metal-Free, Mild Protocol to Access 3-Arylsulfenyl Indoles

Abstract

Sulfoximines as S-aryl surrogates permit the preparation of 3-arylsulfenylindoles through reaction with indoles in the presence of I₂ under visible-light irradiation. This environmentally friendly approach is fast, mild, metal-, photocatalyst-, additive-, and oxidant-free, and it provides the desired products in moderate to good yields with a wide substrate scope.

Key words

sulfoximines - S-aryl surrogates - arylsulfenylindoles - green chemistry - metal-free reaction

Publikationsverlauf

Eingereicht: 18. April 2023

Angenommen nach Revision: 07. Juni 2023

Accepted Manuscript online:
07. Juni 2023

Artikel online veröffentlicht:
31. Juli 2023

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• 39 3-[(4-Chlorophenyl)sulfanyl]-1H-indole (3aa); Typical Procedure A clean 20 mL Schlenk tube was charged with sulfoximine 1a (32 mg, 0.1687 mmol, 1.0 equiv), indole (2a; 20 mg, 0.1707 mmol, 1.0 equiv), and I₂ (43 mg, 0.1694 mmol, 1.0 equiv) in EtOH (1 mL). The mixture was stirred at RT under blue LED irradiation (456 nm/50 W) for 10 mins. When the reaction was complete (TLC; reaction time 10–15 min, depending on the substrate), the solvent was removed in vacuo and the product was purified by column chromatography [silica gel (100–200 mesh), 2–10% EtOAc–hexane] to give a white solid; yield: 36 mg (81%); mp 130–131 °C. ¹H NMR (500 MHz, CDCl₃): δ = 8.38 (br s, 1 H), 7.56 (d, J = 8.0 Hz, 1 H), 7.45 (d, J = 3.0 Hz, 1 H), 7.42 (d, J = 8.0 Hz, 1 H), 7.28–7.23 (m, 1 H), 7.16 (td, J = 8.0, 1.0 Hz, 1 H), 7.11–7.08 (m, 2 H), 7.02–6.99 (m, 2 H). ¹³C NMR (126 MHz, CDCl₃): δ = 137.9, 136.6, 130.8, 130.6, 128.9, 128.8, 127.2, 123.3, 121.2, 119.6, 111.8, 102.6. HRMS (ESI): m/z [M + H]⁺ calcd for C₁₄H₁₁ClNS: 260.0295; found: 260.0294.