Photoinduced Construction of Thieno[3,4-c]quinolin-4(5H)-ones/Selenopheno[3,4-c]quinolin-4(5H)-ones Using Diphenyl Disulfide or Diphenyl Diselenide as Sulfur or Selenium Sources

Abstract

A photocatalytic synthesis of thieno­[3,4-c]­quinolin-4­(5H)-ones/selenopheno­[3,4-c]­quinolin-4­(5H)-ones using diphenyl disulfide or diphenyl diselenide as sulfur or selenium sources was developed. Two C–S/Se bonds and one C–C bond were constructed simultaneously without transition metals and other additives.

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

“…Based on radical trapping and literature reports, 18 b , c we proposed a plausible mechanism for this reaction. The homolytic cleavage of PhSSPh ( 2a ) under visible light irradiation 23 leads to the thiyl radical I , which adds to the strained carbon–carbon bond of the BCB 1b to give tertiary radical intermediate II . Subsequent 5- exo -trig cyclization of II generates primary alkyl radical III .…”

Radical cascade cyclization of 1,n-enynes under photo/electrochemical conditions

“…In 2023, Wang reported an alternative cyclization approach of 1,7-enynes 75 to obtain thieno- or selenopheno[3,4- c ]quinolin-4(5 H )-ones 76 with diphenyl disulfide or diphenyl diselenide as sulfur or selenium source, respectively (Scheme 4f). 32 The reaction proceeds through a photoinduced homolytic bond cleavage of diphenyl diselenide to release a selenium-centered radical adding to the C–C double bond. After an intramolecular cyclization with the C–C triple bond and radical attack of the resulting vinyl radical to selenium, the Se–heterocycle is formed.…”

Selectfluor-Mediated Electrophilic Annulation of 2-Alkynyl Biaryls with Diorganyl Diselenides

“…A diversity of selanylation reactions with diorganyl diselenides as the selenium source have been reported over the past years . In general, these selanylation reactions can be divided into two categories according to the reactive intermediate: the organyl selenium radical and the organyl selenium cation …”