Catalyst‐Free Photoredox Addition–Cyclisations: Exploitation of Natural Synergy between Aryl Acetic Acids and Maleimide

Manley, David W.; Mills, Andrew; O’Rourke, Christopher; Slawin, Alexandra M. Z.; Walton, John C.

doi:10.1002/chem.201304929

Cited by 12 publications

(19 citation statements)

References 67 publications

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“…Under similar conditions, intramolecular additions have been also performed . A comprehensive study was also recently published on an uncatalyzed version of the reaction . A competition between simple addition and addition cyclization was also observed in the transformation of α,β‐unsaturated carbonyl compounds with aniline derivatives .…”

Section: Photoredox Catalytic Reactionsmentioning

confidence: 99%

Electron and hydrogen transfer in organic photochemical reactions

Hoffmann

2014

J of Physical Organic Chem

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Electron and hydrogen transfers are basic steps in many chemical reactions. Photochemical or electronic excitation significantly influences the reactivity of chemical compounds and thus also these transfer processes. Furthermore, the formation of typical intermediates has a decisive impact on the outcome of the transformations. Based on these properties of photochemical processes, efficient homogeneous and heterogeneous photocatalytic transformations for application to organic synthesis have been developed. Efficient reactions without any chemical activation but induced by photochemical electron transfer can also be carried out. The photon acts as a traceless reagent. In the context of photochemical hydrogen transfer, two processes are frequently encountered. The two particles the electron and the proton are transferred either simultaneously or in two steps. In the latter case, the electron is transferred first and the proton follows. Both processes are applied to organic synthesis. Copyright © 2014 John Wiley & Sons, Ltd.

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Section: Photoredox Catalytic Reactionsmentioning

confidence: 99%

Electron and hydrogen transfer in organic photochemical reactions

Hoffmann

2014

J of Physical Organic Chem

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“…[96] The same reaction was also observed under UV irradiation and without a photoredox catalyst. [97] Under these conditions, only tandem addition cyclization products were obtained. The photochemical Kolbe reaction catalyzed by TiO 2 is a convenient method to generate alkyl radicals, which undergo typical reactions such as dimerization.…”

Section: C-c Bond Formationmentioning

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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“…1 H NMR (CDCl 3 ): δ 3.74 (s, 6H), 3.78 (s, 3H), 3.79 (s, 3H), 5.34 (d, 1H, J = 5.0 Hz), 5.54 (d, 1H, J = 5.0 Hz), 6.58−7.28 (m, 11H). 13 (52). 52 was obtained from 17 according to general method IIIA.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%