Visible Light-Induced Synthesis of Sulfenamides via Oxidative Coupling of Amines with Thiols

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 4, 2025

Herein, we report a visible light-induced synthesis of sulfenamides via the oxidative coupling amines with thiols using O2 as an oxidant. The photoreaction was conducted under simple and mild conditions, without any photocatalysts, metals, or additives. Detailed mechanistic studies revealed that sulfur radical is generated through single-electron transfer from in situ-generated anion to light irradiation. This intermediate couples form disulfide, which subsequently undergoes aminolysis produce sulfenamides.

Language: Английский

Iodine/DMF-Mediated Regioselective Sulfenylation Using Arenediazonium Tosylates and Sodium Metabisulfite: An Easy Access to 3-Arylthioindoles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(20), P. 15075 - 15082

Published: Oct. 9, 2024

A practical C3 sulfenylation of indoles has been accomplished using arenediazonium tosylates and sodium metabisulfite, with a key role iodine/DMF combination in the reaction. The method involves scarce use metabisulfite as divalent sulfur source offers an array structurally diverse 3-arylthioindoles high yields under operationally simple transition-metal-free mild conditions.

Language: Английский