Synthesis and Application Dichalcogenides as Radical Reagents with Photochemical Technology

Abstract

Dichalcogenides (disulfides and diselenides), as reactants for organic transformations, are important and widely used because of their potential to react with nucleophiles, electrophilic reagents, and radical precursors. In recent years, in combination with photochemical technology, the application of dichalcogenides as stable radical reagents has opened up a new route to the synthesis of various sulfur- and selenium-containing compounds. In this paper, synthetic strategies for disulfides and diselenides and their applications with photochemical technology are reviewed: (i) Cyclization of dichalcogenides with alkenes and alkynes; (ii) direct selenylation/sulfuration of C−H/C−C/C−N bonds; (iii) visible-light-enabled seleno- and sulfur-bifunctionalization of alkenes/alkynes; and (iv) Direct construction of the C(sp)–S bond. In addition, the scopes, limitations, and mechanisms of some reactions are also described.

Strain-enabled radical spirocyclization cascades: rapid access to spirocyclobutyl lactones and – lactams

“…Next, we turned our attention to employing diphenyl disulfide 2a, which is known to add to unsaturated compounds and strained carbon–carbon bonds and can also capture carbon radicals. 18 …”

A Novel Fluorescent Probe containing dihydropyrimidinone Analogue for Highly Sensitive, Selective Detection of Al(III) Ions with its Molecular Docking, ADME/T and Anticancer Impact

“…Figure 8 illustrates the fluorescence spectra of the studied chemosensor when exposed to varying concentrations of Al(III) ions ranging from 0 to 6×10 −5 M. The chemosensor exhibits emission bands at 592 nm in an EtOH solvent. Upon incremental introduction of diverse concentrations of Al(III) ions to the chemosensor, the fluorescence intensity diminishes, accompanied by a noticeable blue shift of 44 nm in the emission peak [43] . At higher concentrations of metal ions, distinct bands emerge, attributed to the formation of a 1 : 2 ligand‐metal complex, a finding subsequently corroborated by Job′s plot analysis (Figure S1) (at which the mole fraction C L /C L +C M showed maxium at 0.601), and inductively coupled plasma (ICP) analysis.…”

Polyunsaturated sulfur/selenium-containing products based on regio- and stereoselective nucleophilic addition and substitution reactions of 1,2-bis[(Z)-2-(vinylsulfanyl)ethenyl] diselane

“…Diorganyl diselenides are valuable starting materials in various reactions and used as precursors of selenium-containing nucleophilic and electrophilic reagents. 63–65…”

“…Diorganyl diselenides are valuable starting materials in various reactions and used as precursors of selenium-containing nucleophilic and electrophilic reagents. [63][64][65] Methods for the synthesis of vinyl selenides are described in many publications, which are summarized in reviews. 66,67…”