A sustainable photochemical aerobic sulfide oxidation: access to sulforaphane and modafinil

Abstract

Sulfoxide-containing molecules display an important class of compounds in pharmaceutical industry and many efforts have been devised for the development of new and green protocols, targeting the chemoselective transformation of...

Functionalized Benzothiadiazole Non‐Fused A−D−A’−D−A Small Molecules for Effective Electron Mobilities and Metal‐free Photocatalysis

“…Plausible intermediates are well established from previous literature [56][57][58][59][60][61][62][63] and we also presented involvement of possible intermediate in these reactions using reactive intermediate scavengers such as para-benzoquinone (BQ) and 1,4-Diazabicyclo[2.2.2]octane (DABCO). BQ is commonly used to confirm the existence of superoxide ion radicals/hydroperoxyl radicals (O 2 *À /HO 2 * ).…”

Cyrene: a bio-based solvent for the Mizoroki–Heck reaction of aryl iodides

“…32 In our group, over the past years, we focused on developing green and eco-friendly synthetic protocols that are easily applied to the synthesis of naturally occurring products with excellent pharmaceutical profiles, or of pharmaceuticals. 39 In 2007, Li and coworkers isolated a new family of compounds from the methanolic extract of Piper lolot , including piperlotine A, piperlotine C, piperlotine D and 1- trans -cinnamoylpyrrolidine (Scheme 2), which showed potent antiplatelet aggregation activity. 40 Also, their cytotoxic activity and antimicrobial activity were noted.…”

3H‐Phenothiazin‐3‐one: A Photocatalyst for the Aerobic Photochemical Oxidation of Sulfides to Sulfoxides

“…[35] In accordance with literature, the addition of H 2 O led to an acceleration of the reaction, while suppressing overoxidation to sulfone, probably via hydrogen bond formation. [16,36,37] 2-Me-THF was not a suitable solvent (Table 1, entry 10), [17] while benzene or dimethyl sulfoxide also did not afford the desired product (Table 1, entries 11 and 12). [35] Other alcohols used as the solvent did not afford results similar to methanol (Table 1, entries 13-15).…”

“…[13] In the same vein, a 2,5diketopiperazine proline-based organocatalyst has also been effective in an aerobic but not photochemical process, [14] while the Kokotos group has developed various protocols for this transformation, both organocatalytic [15] or photochemical. [16,17] The Kokotos group explored the impact of the irradiation source on sulfide photooxidation and exploited anthraquinone as the photocatalyst developing a series of protocols (Scheme 1, B). [16] Irradiation at 427 nm (anthraquinone protocol) or at 370 nm (catalyst-free protocol) led to sulfide oxidation with a good substrate scope, high yields and chemoselectivities.…”