Abstract
In this study, the reactivity of organochalcogen compounds toward a representative alkyl-lead bond compound under light was investigated in detail. Under light irradiation, the Cy-Pb bond of Cy6Pb2 (Cy = cyclohexyl) undergoes homolytic cleavage to generate a cyclohexyl radical (Cy•). This radical can be successfully captured by diphenyl diselenide, which exhibits excellent carbon-radical-capturing ability. In the case of (PhS)2 and (PhTe)2, the yields of the corresponding cyclohexyl sulfides and tellurides were lower than that of (PhSe)2. This probably occurred due to the low carbon-radical-capturing ability of (PhS)2 and the high photosensitivity of the cyclohexyl-tellurium bond.
Highlights
Organochalcogen compounds are widely used as functional materials and pharmaceuticals [1,2]
By focusing on the radical reaction properties of organochalcogen compounds, we successfully developed a series of new addition reactions based on radical mechanisms [18,19,20,21,22,23,24]
In this paper, we report the novel organic reactions of diaryl dichalcogenides with hexacyclohexyldilead under photoirradiation to produce aryl cyclohexyl monochalcogenides. (PhSe)2 showed a high carbon-radical-capturing ability toward the cyclohexyl radicals generated from heavier-element compounds
Summary
Organochalcogen compounds are widely used as functional materials and pharmaceuticals [1,2]. During the course of this study, we found that selenium and tellurium compounds have excellent carbon-radical-trapping abilities This observation prompted us to investigate the radical reactions of heavier elements in groups 14 and 15. The thermal reaction of 1 with TEMPO suggests that cyclohexyl radicals were not generated by 1 under heating conditions (Equation (3)). The cyclohexyl radical generated by 1 was successfully trapped by TEMPO, and Cy-TEMPO was formed in good yield as the sole product (Equation (4)). The cyclo5hoefx1y0l radical generated by 1 was successfully trapped by TEMPO, and Cy-TEMPO was formed in good yield as the sole product (equation 4). Several photochemical C-Se bond formation reactions have been reporItnedre[c3e4n–t40y]e.aTrsh,esuevseeroafl pphhoottooccahteamlyisctaslisCo-Sneeboofnthdefoefrfmecattiivoenmreeathctoiodnsstohaacvheiebveeenthriestpyopreteodf t[r3a4n–s4f0o]r.mTahteiounsuenodfeprhvoistiobclaetalilgyhstsirirsadoinaetionf t[h3e4,e3f5f]e.cPtihvoetomcaetahloydsts-ftroeeacCh-iSeevbeotnhdis ftoyrpme aotfiotrnanresfaocrtmioantsiounnudnerdeUrVvAisi[b3l8e]loigrhvtiisrirbaldeilaigtihotn[[3364,,3375,]3.9P]hirortaodcaiatatiloynsth-farvee Cal-sSoe beoennd rfeoprmoratetido,nbruetaactnioonxsiduanndte(rOU2)VoAr a[3b8a] soerivsiosifbtelen lnigehedt [e3d6.,3T7h,3e9p] rierrsaednitarteioanctihoanvpe raolvsoidbeesean nrepworatned,sbimutpalenpohxoidtoacnhte(mOi2c)aol rCa-Sbeabsoenisdofoftremnanteioenderdea. cTtihoenpwreitsheonut treaapcthiotnocpartoavlyidset sora anebwasea.nd simple photochemical C-Se bond formation reaction without a photocatalyst or a base
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