The reaction of α-phenethyl radicals with 1,4-benzoquinone and 2,6-di-tert-butyl-1,4-benzoquinone

Engel, Paul S.; Park, Hee Jung; Mo, Hua; Duan, Shaoming

doi:10.1016/j.tet.2010.09.034

Cited by 11 publications

(9 citation statements)

References 97 publications

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“…Later,E ngel and co-workers carriedo ut detailed investigations into the reactiono fa-phenethyl radicals with BQ and 2,6-di-tert-butyl-1,4-benzoquinone. [21] Azo-a-phenylethane 16 was utilized as ag ood source of a-phenethyl radicals. Notably, the absolute rate constant for BQ irreversibly trapping a-phenethyl radicals has been determinedt ob e4 .4 10 6 m À1 s À1 at 43 8C[Eq.…”

Section: Alkyl Radical Additionmentioning

confidence: 99%

“…[28] With molecular iodine as the effective catalyst, TBPB or tert-butyl hydroperoxide( TBHP;7 0% aqueous solution) as the oxidant,a nd NaOAc as the additive,d ifferents ubstituted dihydrofurans and indolizines could be obtainedi n good yields [Eqs. (21) and (22);E WG = electron-withdrawing group].N otably,t his reaction could be easily scaled up, demonstrating ap owerful methodf or heterocycle synthesis. Mechanistics tudies showed that both iodiner adical and hypervalent iodine species were likely to be involved during the reaction system.…”

Section: Alkyl Radical Additionmentioning

confidence: 99%

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Carbon‐Centered Radical Addition to C=X Bonds for C−X Bond Formation

Liu

Lei

2015

Chemistry An Asian Journal

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Among various kinds of radical reactions, the addition of carbon-centered radicals to unsaturated bonds represents a powerful tool for the construction of different C-C and C-X (X = N, O, S, etc.) bonds, in which typically applied unsaturated bonds include alkenes, alkynes, imines, carbonyls, and even thiocarbonyls. When C=X bonds are utilized as the radical acceptors, reactions usually occur at the carbon position to generate a heteroatom radical, during which C-C coupling products are formed. This reaction mode has dominated this field for several decades. However, there is also another unconventional type of radical addition mode, in which carbon-centered radicals attack the heteroatom position of C=X bonds to generate carbon radicals, during which selective C-X bond formation is achieved. This reaction mode demonstrates an effective method for the construction of different C-X bonds, such as C-O, C-N, and C-S bonds. This Focus Review gives an overview of recent advances in this unconventional field.

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Section: Alkyl Radical Additionmentioning

confidence: 99%

Section: Alkyl Radical Additionmentioning

confidence: 99%

Carbon‐Centered Radical Addition to C=X Bonds for C−X Bond Formation

Liu

Lei

2015

Chemistry An Asian Journal

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“…[9] Cyclization of cation II with a second olefin followed by deprotonation yields the final product and regenerates the HOTf catalyst. [10] Oxidation of radical VI by BQ/HOTf gives the final product and regenerates the HOTf catalyst. Radical IV then isomerizes into radical V and cyclizes with a second olefin to generate radical VI.…”

Section: Methodsmentioning

confidence: 99%

Trifluoromethanesulfonic Acid Catalyzed Synergetic Oxidative/[3+2] Cyclization of Quinones with Olefins

et al. 2013

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“…Radical IV then isomerizes into radical V and cyclizes with a second olefin to generate radical VI. [10] Oxidation of radical VI by BQ/HOTf gives the final product and regenerates the HOTf catalyst. [9] Based on this mechanistic understanding, we realized that the present method could also be used for the synthesis of asymmetric tetrahydrobenzodifurans through the cyclization of benzoquinone with two different olefins.…”

Section: Methodsmentioning

confidence: 99%