Thiaporphyrin-mediated photocatalysis using red light

Lee, JinGyu; Papatzimas, James W.; Bromby, Ashley D.; Gorobets, Evgueni; Derksen, Darren J.

doi:10.1039/c6ra11374e

Cited by 27 publications

(22 citation statements)

References 36 publications

(12 reference statements)

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“…For instance, König and Zeitler demonstrated that a combination of eosin Y (OD13) with a sacrificial electron donor can trigger the reductive debromination of several α-carbonyl halides [53]. Riboflavin (OD11) [54] and thiaporphyrin [55] have been applied as well as organic photocatalysts for similar reductive dehalogenations.…”

Section: Methodsmentioning

confidence: 99%

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Amos¹,

Garreau²,

Buzzetti³

et al. 2020

Beilstein J. Org. Chem.

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Organic dyes have emerged as a reliable class of photoredox catalysts. Their great structural variety combined with the easy fine-tuning of their electronic properties has unlocked new possibilities for the generation of reactive intermediates. In this review, we provide an overview of the available approaches to access reactive intermediates that employ organophotocatalysis. Our contribution is not a comprehensive description of the work in the area but rather focuses on key concepts, accompanied by a few selected illustrative examples. The review is organized along the type of reactive intermediates formed in the reaction, including C(sp3) and C(sp 2 ) carbon-, nitrogen-, oxygen-, and sulfur-centered radicals, open-shell charged species, and sensitized organic compounds.

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Section: Methodsmentioning

confidence: 99%

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Amos¹,

Garreau²,

Buzzetti³

et al. 2020

Beilstein J. Org. Chem.

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“…Porphyrins containing other heteroatoms present physicochemical and electronic properties that are quite different from regular N 4 -porphyrins. These structures absorb and emit light at lower energies, as for example the thiaporphyrins that absorb beyond 650 nm [8,28]. Derksen and co-workers studied bond-cleavage reactions that can occur in biological microenvironments, using a light source with wavelengths frequently employed in photomedicine (650-850 nm) and thiophene-containing porphyrins [28].…”

Section: Review Porphyrins As Photoredox Catalystsmentioning

confidence: 99%

“…These structures absorb and emit light at lower energies, as for example the thiaporphyrins that absorb beyond 650 nm [8,28]. Derksen and co-workers studied bond-cleavage reactions that can occur in biological microenvironments, using a light source with wavelengths frequently employed in photomedicine (650-850 nm) and thiophene-containing porphyrins [28]. The authors reported that meso-5,10,15,20-tetraphenyl-21-monothiaporphyrin (STPP), combined with Hantzsch ester (HEH) and N,N-diisopropylethylamine (DIPEA), promoted the dehalogenation of α-functionalized carbonyl-containing compounds under red light (λ > 645 nm) in a reductive quenching.…”

Section: Review Porphyrins As Photoredox Catalystsmentioning

confidence: 99%

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

Silva

Bartolomeu

et al. 2020

Beilstein J. Org. Chem.

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In this review we present relevant and recent applications of porphyrin derivatives as photocatalysts in organic synthesis, involving both single electron transfer (SET) and energy transfer (ET) mechanistic approaches. We demonstrate that these highly conjugated photosensitizers show increasing potential in photocatalysis since they combine both photo- and electrochemical properties which can substitute available metalloorganic photocatalysts. Batch and continuous-flow approaches are presented highlighting the relevance of enabling technologies for the renewal of porphyrin applications in photocatalysis. Finally, the reaction scale in which the methodologies were developed are highlighted since this is an important parameter in the authors’ opinion.

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“…10 Later, the Derksen group introduced a red-light-induced photoreductive dehalogenation mediated by the thiaporphyrin 3b (Scheme 1b). 11 Afterwards, the Shibata group revealed a trifluoromethylation of alkenes and alkynes under red-light irradiation, mediated by the trifluoroethoxy-coated subphthalocyanine 3c (Scheme 1c). 12 Recently, in a related process, the Postigo group reported a fluoroalkylation reaction of (het)aromatics and sulfides with perfluoroalkyl iodides under red LED illumination employing zinc phthalocyanine dye (3d) as a PC (Scheme 1d).…”

Section: Red-light-induced Photocatalysismentioning

confidence: 99%

Helical Carbenium Ion-Based Organic Photoredox Catalyst: A Versatile and Sustainable Option in Red-Light-Induced Reactions

Mei

Gianetti

2020

Synlett

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The development of a sustainable catalytic system for red-light-induced photocatalysis is presented. The catalytic system consists of a helical carbenium ion-based organic photoredox catalyst (PC) that is capable of using low-energy red light (λmax = 640 nm) for both photooxidations and photoreductions. Its successful applications in the aerobic oxidative hydroxylation of arylboronic acids and in the oxidation of benzylic C(sp3)–H bonds (reductive quenching), as well as in dual transition-metal/organocatalyzed C–H arylations and intermolecular atom-transfer radical additions (oxidative quenching) provide further support for its role as a versatile and efficient organic PC.1 Introduction2 Red-Light-Induced Photocatalysis3 Properties of N,N′-Dipropyl-1,13-dimethoxyquinacridinium Tetrafluoroborate4 Two Proposed Representative Catalytic Cycles of [ n Pr-DMQA+][BF4 –]5 Applications of [ n Pr-DMQA+][BF4 –] in Red-Light-Induced Photocatalysis6 Conclusion

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Thiaporphyrin-mediated photocatalysis using red light

Abstract: Thiophene-containing porphyrin compounds are capable of catalytic, photo-reductive dehalogenation on an array of α-halo ketone model substrates with low catalyst loadings (0.1 mol%), in the presence of low energy, red light (>645 nm).

Cited by 27 publications

References 36 publications

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

Helical Carbenium Ion-Based Organic Photoredox Catalyst: A Versatile and Sustainable Option in Red-Light-Induced Reactions

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