Azide/oxygen photocatalysis with homogeneous and heterogeneous photocatalysts for 1,2-aminohydroxylation of acyclic/cyclic alkenes and Michael acceptors

Griesbeck, Axel G.; Steinwascher, Jörg; Reckenthäler, Melissa; Uhlig, Johannes

doi:10.1007/s11164-012-0629-3

Cited by 12 publications

(5 citation statements)

References 20 publications

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“…Griesbeck and co-workers have explored a unique alkene difunctionalization reaction in a series of investigations on azidohydroperoxidation facilitated by PET. − In an initial report, Rhodamine B ( RhBH-Cl ) was utilized as a photoredox catalyst in the transformation along with sodium azide (NaN 3 ) under aerobic conditions, which yielded a mixture of alcohols 168.3 and hydroperoxides 168.2 as products (Scheme ). The crude photolysis mixtures were treated with sodium sulfite (Na 2 SO 3 ) to give the alcohols 168.4 – 168.7 in greater than 90% yield.…”

Section: Rhodaminesmentioning

confidence: 90%

Organic Photoredox Catalysis

2016

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In this review, we highlight the use of organic photoredox catalysts in a myriad of synthetic transformations with a range of applications. This overview is arranged by catalyst class where the photophysics and electrochemical characteristics of each is discussed to underscore the differences and advantages to each type of single electron redox agent. We highlight both net reductive and oxidative as well as redox neutral transformations that can be accomplished using purely organic photoredox-active catalysts. An overview of the basic photophysics and electron transfer theory is presented in order to provide a comprehensive guide for employing this class of catalysts in photoredox manifolds.

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Section: Rhodaminesmentioning

confidence: 90%

Organic Photoredox Catalysis

2016

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“…The latter process proceeds with a high degree of atom economy [ 16 ]. We have recently demonstrated this for the azido-hydroperoxidation of alkenes, a convenient method for the synthesis of 1,2-amino alcohols [ 17 – 18 ]. In the field of C–C coupling reactions, the direct hydroxyalkylation of carbonyl compounds and carbonyl analogs is a demanding task because the α-CH activation of alcohols must occur in the presence of the acidic and nucleophilic hydroxy group.…”

Section: Introductionmentioning

confidence: 99%

Homogeneous and heterogeneous photoredox-catalyzed hydroxymethylation of ketones and keto esters: catalyst screening, chemoselectivity and dilution effects

Griesbeck¹,

Reckenthäler²

2014

Beilstein J. Org. Chem.

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SummaryThe homogeneous titanium- and dye-catalyzed as well as the heterogeneous semiconductor particle-catalyzed photohydroxymethylation of ketones by methanol were investigated in order to evaluate the most active photocatalyst system. Dialkoxytitanium dichlorides are the most efficient species for chemoselective hydroxymethylation of acetophenone as well as other aromatic and aliphatic ketones. Pinacol coupling is the dominant process for semiconductor catalysis and ketone reduction dominates the Ti(OiPr)4/methanol or isopropanol systems. Application of dilution effects on the TiO2 catalysis leads to an increase in hydroxymethylation at the expense of the pinacol coupling.

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“…Similar transformations have also been carried out using homogeneous photocatalysis. [56] Reductions Although less known, a variety of reduction reactions can be carried out using photocatalysis with titanium dioxide. [57] Carbonyl compounds are reduced to alcohols.…”

Section: Oxidationsmentioning

confidence: 99%

Photocatalysis with TiO2 Applied to Organic Synthesis

Hoffmann

2015

Aust. J. Chem.

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Titanium dioxide is a versatile heterogeneous catalyst. Absorption of light by a TiO2 particle leads to the formation of an electron–hole pair. Electron transfer from or to the particle induces redox reactions. Although mainly applied in the context of environmental chemistry, these processes are also used to selectively transform organic compounds. Oxidations and reductions have been carried out. Applications to the synthesis of heterocycles have been reported. Many C–C bond formation reactions have been performed. Owing to adsorption of the substrates or by different surface modifications, visible light can be used to excite the catalytic system, which generates mild reaction conditions.

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Azide/oxygen photocatalysis with homogeneous and heterogeneous photocatalysts for 1,2-aminohydroxylation of acyclic/cyclic alkenes and Michael acceptors

Cited by 12 publications

References 20 publications

Organic Photoredox Catalysis

Organic Photoredox Catalysis

Homogeneous and heterogeneous photoredox-catalyzed hydroxymethylation of ketones and keto esters: catalyst screening, chemoselectivity and dilution effects

Photocatalysis with TiO2 Applied to Organic Synthesis

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