Anodic Oxidation of Benzenesulfinate Ion.

Persson, Björn; Seita, J.; Holm, Arne; Orazi, Orfeo O.; Schroll, Gustav; Williams, D. H.; Pilotti, Anne‐Marie

doi:10.3891/acta.chem.scand.31b-0088

Cited by 25 publications

(20 citation statements)

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“…Upon visible light irradiation, single electron transfer (SET) from the sodium sulfinate salt (for PhSO 2 . /PhSO 2 Na, E 1/2 red = +0.5 V vs. SCE in MeCN) to the highly oxidizing excited state B of the photocatalyst (PC) would generate the sulfonyl free radical (PhSO 2 . ) along with the reduced form C of the photocatalyst.…”

Section: Introductionsupporting

confidence: 72%

Cascade Cross‐Coupling of Dienes: Photoredox and Nickel Dual Catalysis

et al. 2019

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Chemical transformations based on cascade reactions have the potential to simplify the preparation of diverse and architecturally complex molecules dramatically. Herein, we disclose an unprecedented and efficient method for the cross‐coupling of radical precursors, dienes, and electrophilic coupling partners via a photoredox‐ and nickel‐enabled cascade cross‐coupling process. The cascade reaction furnishes a diverse array of saturated carbo‐ and heterocyclic scaffolds, thus providing access to a quick gain in C−C bond saturation.

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Section: Introductionsupporting

confidence: 72%

Cascade Cross‐Coupling of Dienes: Photoredox and Nickel Dual Catalysis

et al. 2019

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“…10 6 m –1 s –1 ), and must be followed by a radical fragmentation to obtain the desired alkene. In the same event is produced the stabilized phenyl sulfonyl radical, which is easily reduced [ E 1/2 (PhSO 2 · /PhSO 2 – ) = +0.50 V vs. SCE] by the hydroflavin radical [ E 1/2 (RFTA/RFTAH · ) ≈ –0.60 V vs. SCE], thereby closing the catalytic cycle after proton transfer. According to the redox potentials involved, this electron transfer is highly exergonic (ΔG ET ca.…”

Section: Resultsmentioning

confidence: 99%

Direct Decarboxylative Allylation and Arylation of Aliphatic Carboxylic Acids Using Flavin‐Mediated Photoredox Catalysis

2019

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We describe herein a direct decarboxylative allylation of aliphatic carboxylic acids with allylsulfones using visible light and riboflavin tetraacetate (RFTA) as photocatalyst. The reaction proceeds at room temperature tolerating a wide range of functionalities, avoiding the use of external bases or additives. Mechanistic studies support that alkyl radicals are involved in the reaction and that a true photocatalytic cycle is operating. It is proposed that the carboxylic acid is deprotonated by [RFTA]·–, and the corresponding carboxylate acts as a reductive quencher of RFTA*, which after decarboxylation produces the alkyl radical. The methodology was adapted to prepare benzothiazoles substituted at C2, by reacting some carboxylic acids with 2‐(phenylsulfonyl)benzothiazole. The number of carboxylic acids suitable for this arylation was lower than for the allylation and this different reactivity was briefly commented.

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“…Reaction of 5 with a vinyl sulfone would then generate the β-sulfonyl radical 6 , which after elimination of a sulfinyl radical would provide the allylic amine product. Completion of the photocatalytic cycle would then be accomplished via reduction of the sulfinyl radical (For PhSO 2 • /PhSO 2 Na, E 1/2 red = +0.50 V vs SCE) 19 with Ir II 7 ( E 1/2 [Ir III/II ] = −1.37 V vs SCE) 17 to give a sulfinate anion while reconstituting the photocatalyst 1 .…”

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confidence: 99%

Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines

2014

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A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C–H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.

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Anodic Oxidation of Benzenesulfinate Ion.

Cited by 25 publications

References 0 publications

Cascade Cross‐Coupling of Dienes: Photoredox and Nickel Dual Catalysis

Cascade Cross‐Coupling of Dienes: Photoredox and Nickel Dual Catalysis

Direct Decarboxylative Allylation and Arylation of Aliphatic Carboxylic Acids Using Flavin‐Mediated Photoredox Catalysis

Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines

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