Thiol–ene/oxidation tandem reaction under visible light photocatalysis: synthesis of alkyl sulfoxides

Abstract

The photocatalyzed synthesis of sulfoxides from alkenes and thiols has been carried out using Eosin Y.

Selective Photooxidation of Sulfides Catalyzed by Bis‐cyclometalated IrIII Photosensitizers Bearing 2,2′‐Dipyridylamine‐Based Ligands

“…Sulfoxides are very important intermediates in organic synthesis, and some of them are commercialized as drugs owing to their pharmacological activity, for example, alliin, armodafinil, and esomeprazole . Hence, the development of chemoselective and efficient methods of synthesis from the respective sulfides is an appealing challenge .…”

“…[8] Sulfoxides are very important intermediates in organic synthesis, and someo ft hem are commercialized as drugs owing to their pharmacological activity, [2,9,10] for example, alliin, armodafinil, and esomeprazole. [11] Hence, the development of chemoselective and efficient methodso fs ynthesisf rom the respectives ulfides is an appealing challenge. [12,13] Previously, aerobic photooxidation of sulfides has been successfully accomplished by using metal complexes or organic dyes as PSs.…”

Photocatalytic Synthesis of 3‐Sulfanyl‐ and 1,3‐Bis(sulfanyl)indolizines Mediated by Visible Light

“…Based on previous reports on the photocatalyzed formation of C–S bonds via thiyl radical intermediates, 2‐phenylindolizine ( 1a ) and benzenethiol ( 2a ) were chosen as model reagents for optimization of the reaction conditions, in the presence of eosin Y as an inexpensive and readily available dye‐based photocatalyst (Table ). The initial studies were focused on the synthesis of 3‐sulfanylindolizine 3a ; the reaction yields and the composition of the resulting mixtures of products were determined by 1 H NMR analysis, using 1,3,5‐trimethoxybenzene as an internal standard.…”

Photocatalytic formation of carbon–sulfur bonds

“…Very recently, Wei, Wang and co-workers and the working groups of Fraile and Aleman independently reported of visible-light photocatalyzed procedures for the preparation of sulfoxides from the respective sulfides and alkenes by radical thiol–ene reactions ( Scheme 15 ) [ 45 – 46 ].…”