Regioselective peri-C–H selenylation of aromatic compounds with weakly coordinating ketone groups

Abstract

A novel and versatile method for peri-C–H selenylation of aromatic compounds bearing ketone groups, including chromones, xanthones, acridinones, quinolinones and naphthoquinones with diselenides under Ru(II) catalysis is presented. Various chromones...

Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp2)–H and C(sp3)–H bonds

“…Although the transition metal-catalyzed chelation-assisted C(sp 2 )-H chalcogenation has been reviewed in several elegant works, 58,66,68 most of them are concerned about the monochalcogenation and only sporadic examples of dichalcogenation have been discussed. [112][113][114][115][116][117][118][119][120][121][122][123][124][125][126][127][128][129][130] Generally, the outcomes of mono-/dichalcogenation are determined by the intrinsic electronic and steric properties of substrates. However, selective mono-/dichalcogenation could be achieved by controlling the reagent loadings, the types of solvents/bases, and a combination of various factors.…”

C−H Functionalization of Aldehydes and Ketones with Transient Directing Groups: Recent Developments

“…Moreover, although ketones have a weak coordinating ability and required generally harsh conditions for CÀ H activation, they are less sensitive than aldehydes so can be more often used as real DG. [34] However, some examples of C(sp 2 )À H activation of ketones based on a TDG strategy have been reported. Previously, arylation or amidation reactions were described and, in 2021, Lou and Xu disclosed a palladiumcatalyzed fluorination of aromatic ketones 58 with methyl carbamate to form a TDG (Scheme 17).…”

Visible-light-mediated selenylation/cyclization reactions of diselenide with acrylimide derivatives: synthesis of selenosubstituted pyrrolidine-2,5-diones

“…In the past few decades, chemists have made great efforts to apply diselenides in organic synthesis, 7–9 but most of the reported cyclization reactions involving selenium radicals as sources of diselenides rely on metal catalysts. 10,11 In 2019, Sun and coworkers reported the selenodifluoromethylation of alkenes under oxidation conditions, which constructed a series of structurally diverse 4-seleno-α,α-difluoro-γ-lactams through radical tandem cyclization/selenylation and selenium radicals were produced under copper-catalyzed conditions (Scheme 1a). 12 Selenium radical production from diselenides under visible light irradiation serves as an important strategy for the synthesis of organoselenium compounds.…”