Upconversion of Reductants

Syroeshkin, Mikhail A.; Kuriakose, Febin; Saverina, Evgeniya A.; Timofeeva, Vladislava A.; Egorov, Mikhail P.; Alabugin, Igor V.

doi:10.1002/anie.201807247

Cited by 75 publications

(61 citation statements)

References 164 publications

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“…To the best of our knowledge, this is the first example where a neutral organic super electron donor has been used in a catalytic cycle. Viewed from a more general perspective, we have shown how a suitable heterocycle can react with a mild hydridic reducing agent to access a highly reducing intermediate …”

Section: Methodsmentioning

confidence: 99%

Neutral Organic Super Electron Donors Made Catalytic

et al. 2019

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Neutral organic super electron donors (SEDs) display impressive reducing power but, until now, it has not been possible to use them catalytically in radical chain reactions. This is because, following electron transfer, these donors form persistent radical cations that trap substrate‐derived radicals. This paper unlocks a conceptually new approach to super electron donors that overcomes this issue, leading to the first catalytic neutral organic super electron donor.

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Section: Methodsmentioning

confidence: 99%

Neutral Organic Super Electron Donors Made Catalytic

et al. 2019

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“…In this case, molecular oxygen worked as the oxidant and only t BuOK in DMF solution was used . This reaction proceeded through reductant up‐conversion including C−H bond activation, which lowers the Gibbs free energy of the intramolecular C−N bond formation …”

Section: Intramolecular Covalent Bond Formation Through the Oxidationmentioning

confidence: 99%

Synthesis of π‐Functional Molecules through Oxidation of Aromatic Amines

Hiroto

2019

Chemistry An Asian Journal

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In this review,w ef ocus on the synthesiso fp-conjugated functional molecules by the oxidation of aromatic amines, which is one of the most effective methods fort he constructiono fC ÀC, CÀN, and NÀNb onds between two pconjugated molecular units,a nd consider their characteristics and applications. Polyanilines are the most common products of the oxidation of aromatic amines;h owever,a zobenzenes, phenazines, and 1,1'-binaphthyl-2,2'-diaminesm ay be produced in this manner also, depending on the reaction conditions. Recent advances in the methodology of aniline oxidation have led to the development of high-regioselectivity industrial-scale syntheses of optically or electroactive pfunctional dyes containing nitrogen atoms. In particular,t he regioselective fusion of p-extended aromatic amines can be used to prepare distorted p-conjugated molecules under mild reactionc onditions, allowing the construction of unprecedented curved nitrogen-containing p-conjugated molecules.Scheme1.Aniline oxidations.Scheme2.Reactionpathways for aniline oxidation.[a] Prof.

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“…This strategy finds numerous applications in chemistry. 41,42 In this section, we will compare the two such "thermodynamic auxiliaries", CO2 and SO2, and show that they are dramatically different.…”

Section: The Gaseous Co-product Stability: Co2 Vs So2mentioning

confidence: 99%

CO2 or SO2: Should It Stay or Should It Go?

Gomes

Wimmer²,

Smith³

et al. 2019

Preprint

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A broad computational analysis of carbon-centered radical formation via the loss of either CO2 or SO2 from the respective RXO2 radical precursors (X = C or S) reveals dramatic differences between these two types of dissociative processes. Whereas the C-C scission with the loss of CO2 is usually exothermic, the C-S scission with the loss of SO2 is generally endothermic. However, two factors can make the C-S scissions thermodynamically favorable: increased entropy, characteristic for the dissociative processes, and stereoelectronic influences of substituents. The threshold between endergonic and exergonic C-S fragmentations depends on subtle structural effects. In particular, the degree of fluorination in a radical precursor has a notable impact on the reaction outcome. This study aims to demystify the intricacies in reactivity regarding the generation of radicals from sulfinates and carboxylates, as related to their role in radical cross-coupling.

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Upconversion of Reductants

Cited by 75 publications

References 164 publications

Neutral Organic Super Electron Donors Made Catalytic

Neutral Organic Super Electron Donors Made Catalytic

Synthesis of π‐Functional Molecules through Oxidation of Aromatic Amines

CO2 or SO2: Should It Stay or Should It Go?

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