Visible Light‐Mediated Metal‐Free Synthesis of Vinyl Sulfones from Aryl Sulfinates

Abstract

Visible light ande osin Yc atalyze the synthesis of vinyl sulfonesf rom aryl sulfinates and alkenes by ap hotoredox process.T he reactions cope is broad in aryl sulfinates and alkenes and the general and simple procedure providesametal-free alternative for the synthesis of synthetically valuable vinyl sulfones.

Organic Photoredox Catalysis

“…429 This photoredox catalyzed process is possible with Ru(bpy) 3 + or Ir(ppy) 2 (dtb-bpy) + , but eosin Y (EY-Na 2 , 10 mol %) gave a slightly better yield. This net oxidative …”

Organic Reactions Promoted by Metal-Free Organic Dyes Under Visible Light Irradiation

“…Eosin Y (EY) is the typical organic dye to induce the synthetically useful photoredox transformations [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]. EY that absorbed visible light populates in the lowest excited singlet state.…”

“…The vinyl sulfones were synthesized by the EY-catalyzed reaction of alkenes with sodium aryl sulfinates [21]. The reaction of 1,2-dihydronaphthalene 6 with sodium benzenesulfinate 5 was performed in the presence of EY (10 mol%) and nitrobenzene as a terminal oxidant (Figure 3).…”

Recent advances in the synthesis of vinyl sulfones

“…Using green light, the organic dye eosin Y as photocatalyst and nitrobenzene as the terminal oxidant, König and co-workers 43 recently demonstrated the visible light-mediated synthesis of vinyl sulfone scaffolds from olefins with aryl sulfinates (Scheme 23). The reaction allows the conversion of a variety of aryl sulfinates and 1,2-dihydronaphthalene.…”