Selective photocatalytic epoxidation of cyclooctene by molecular oxygen in the presence of porphyrin sensitizers

Hajimohammadi, Mahdi; Bahadoran, Farzad; Davarani, Saied Saeed Hosseiny; Safari, Nasser

doi:10.1007/s11144-009-0121-2

Cited by 7 publications

(14 citation statements)

References 26 publications

(31 reference statements)

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“…Reflections collected 2358 According to earlier works 12 and more recent studies, 13,27,28 axial ligands in aqueous systems. 11,12 In the latter case the Mn(II) species formed in the primary photochemical step (Eq.…”

Section: -7mentioning

confidence: 99%

“…13 Photocatalytic oxygenation of cycloalkenes 12,13,14 and other unsaturated heteroaromatics 5 was achieved by application of both metalated and free-base porphyrins. 5,12,13,14 These precedents inspired us to study the porphyrin-mediated photocatalytic oxygenation of 2,3-[3,2-b-furo]-6,7-benzobicyclo[3.2.1]octa-2,6-diene (1) (see in Fig. 1), 15 the structure of which represents the basic skeleton of many biologically active and important substances isolated from nature.…”

Section: Introductionmentioning

confidence: 99%

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Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic oxygenation of thiophene and furan derivatives: The impact of the type and position of the heteroatom

Vuk

Kikaš

Molčanov

et al. 2014

Journal of Molecular Structure

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Photocatalytic oxygenations of a furan and two thiophene derivatives of benzobicyclo[3.2.1]octadiene have been realized by using anionic and cationic manganese(III) porphyrins as catalysts. The replace of oxygen with sulfur in the heteroaromatic ring considerably decreased the reactivity of these heterocyclic compounds, probably due to the increased aromaticity. The end-products of the oxygenation of the thiophene derivatives significantly deviated from most of those formed from the corresponding furan compounds; the lower reactivity of the thiophene ring enhanced the role of the out-of-ring carbon atom in the reaction pathways. Besides, deviating from the behavior of the furan compounds, the types of the end-products formed from the corresponding thiophene derivatives did not depend on the charge of the photocatalyst, neither on the oxygen concentration. However, also in this case, the position of the heteroatom in the aromatic ring strongly affects the formation of the end-products.

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Section: -7mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic oxygenation of thiophene and furan derivatives: The impact of the type and position of the heteroatom

Vuk

Kikaš

Molčanov

et al. 2014

Journal of Molecular Structure

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“…Similarly to the oxygenation of cycloalkenes, 4,6,16,17 (P)Mn IV =O and (P)Mn V =O intermediates are suggested to the most important in situ generated reactive species in these systems. The primary step in this process is a photoinduced LMCT (ligand-to-metal charge transfer) from axially coordinated hydroxide ligands in aqueous systems (Eq.…”

Section: Discussionmentioning

confidence: 99%

“…Thus, cycloalkenes 4,5,6 and some unsaturated heteroaromatics 7 were successfully functionalized in these reactions. While freebase porphyrins can be utilized as sensitizers for the generation of singlet oxygen, 7,8,9,10,11 water-soluble metalloporphyrins can offer a wider profile of reaction mechanisms, depending on their charge, the solvent, and the substrate to be oxygenated.…”

Section: Introductionmentioning

confidence: 99%

Functionalization of the benzobicyclo[3.2.1] octadiene skeleton possessing one isolated double bond via photocatalytic oxygenation

Vuk

Horváth

Marinić

et al. 2016

Journal of Molecular Structure

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“…Stochiometric amounts of a strong oxidant are needed for the generation of metalloporphyrins [74]. The photosensitized production of singlet oxygen has significance in the photooxidation of organic compounds, DNA damage, and photodynamic therapy [75][76][77], such that a variety of these photosensitizers have been developed and extensively studied [78][79][80][81][82][83].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of benzoins to benzils in the presence of porphyrin sensitizers by air and sunlight or visible light

et al. 2013

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In this work, two new aerobic routes are introduced for the oxidation of a variety of benzoins to benzils by using molecular oxygen in the presence of porphyrins as sensitizers, using white light or sunlight in acetonitrile under mild conditions. The methods have a wide range of applications, do not involve cumbersome work-up, exhibit chemoselectivity and proceed under mild reaction conditions. The resulting products are obtained in good yields in a reasonable time.

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Selective photocatalytic epoxidation of cyclooctene by molecular oxygen in the presence of porphyrin sensitizers

Cited by 7 publications

References 26 publications

Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic oxygenation of thiophene and furan derivatives: The impact of the type and position of the heteroatom

Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic oxygenation of thiophene and furan derivatives: The impact of the type and position of the heteroatom

Functionalization of the benzobicyclo[3.2.1] octadiene skeleton possessing one isolated double bond via photocatalytic oxygenation

Oxidation of benzoins to benzils in the presence of porphyrin sensitizers by air and sunlight or visible light

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