Carbon radical addition–cyclization reaction induced by ruthenium-photocatalyst under visible light irradiation

Yoshioka, Eito; Kohtani, Shigeru; Tanaka, Eri; Hata, Yukari; Miyabe, Hideto

doi:10.1016/j.tet.2014.12.068

Cited by 25 publications

(10 citation statements)

References 123 publications

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“…In principle, the reactions using strictly neutral species are not affected by water. Therefore, the employment of uncharged radical species facilitates the construction of carbon–carbon bonds in aqueous media. , Recently, we studied the viability of ruthenium photocatalyst, Ru(bpy) 3 Cl 2 ·6H 2 O, in the aqueous-medium perfluoroalkyl radical reactions . As a part of our studies on the radical reactions, we started to study the rhodamine B-catalyzed radical reactions in aqueous media.…”

Section: Resultsmentioning

confidence: 99%

Aqueous-Medium Carbon–Carbon Bond-Forming Radical Reactions Catalyzed by Excited Rhodamine B as a Metal-Free Organic Dye under Visible Light Irradiation

et al. 2016

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The utility of rhodamine B as a water-soluble organic photocatalyst was studied in the cascade radical addition-cyclization-trapping reactions under visible light irradiation. In the presence of (i-Pr)2NEt, the electron transfer from the excited rhodamine B to perfluoroalkyl iodides proceeded smoothly to promote the carbon-carbon bond-forming radical reactions in aqueous media. When i-C3F7I was employed as a radical precursor, the aqueous-medium radical reactions proceeded even in the absence of (i-Pr)2NEt. In these reactions, the direct electron transfer from the excited singlet state of rhodamine B would take place. Furthermore, the cleavage of the C-I bond in less reactive i-PrI could be achieved by the reductive electron transfer from the excited rhodamine B, which was confirmed by the fluorescence quenching of rhodamine B with the addition of i-PrI.

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Section: Resultsmentioning

confidence: 99%

Aqueous-Medium Carbon–Carbon Bond-Forming Radical Reactions Catalyzed by Excited Rhodamine B as a Metal-Free Organic Dye under Visible Light Irradiation

et al. 2016

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“…Among the aryldiazonium salts examined, 4‐MeOC 6 H 4 N 2 BF 4 displayed the highest reactivity, while the common radical initiator AIBN had no effect on the reaction. In related studies, a radical addition/cyclization 1,6‐dienes in aqueous media using visible‐light photoredox catalysis was demonstrated by Miyabe …”

Section: The Synthesis Of N‐containing Heterocyclic Ringsmentioning

confidence: 95%

Synthesis ofN-Containing Heterocyclic Compounds Using Visible-light Photoredox Catalysis

Zhou

Hossain

Xiao

2016

The Chemical Record

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Nitrogen heterocycles represent a highly important class of compounds which are widely used in materials science, agrochemistry, and medicinal chemistry. Therefore, there is continuing interest in the development of convenient, efficient, and environmentally benign synthetic methods for the construction of nitrogen containing heterocycles. Due to its natural abundance, ease of use, and promising application in industry, the use of visible light as a driving force for chemical reactions has received considerable attention in the past few years. This account summarizes the synthesis of N-heterocycles using visible-light photoredox catalysis published in the last two years, according to the size and type of the formed N-heterocyclic rings. In the context of seminal works of others in this area, a concise summary of the contributions of the authors is also offered.

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“…Finally, the desired product was delivered by 7 after abstracting a H‐atom from 4 . Another work of synthesizing five‐membered N‐heterocycles via photoinduced C‐radical addition/cyclization cascade of 1,6‐dienes was reported by Miyabe in 2015 …”

Section: Synthesis Of Monocyclic Ringsmentioning

confidence: 99%

Synthesis of Cyclic Compounds via Photoinduced Radical Cyclization Cascade of C=C bonds

Zhao

Xia

2018

The Chemical Record

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Cyclic compounds constitute a great important class of substances in the science of medicine and biology, which renders the research on facile and efficient construction of such complex scaffolds from simple starting materials to be hot and appealing. Recently, the radical cascade reaction involving multiple bond formation/cleavage has emerged as an ideal and powerful route to give high-value cyclic products, along with diminished cost and waste. As a simple and benign methodology, photoredox catalysis offers a readily available access to the generation of radical species. Alkenes have been recognized as one of the most valuable building blocks for the reason they allow installation of different functional groups simultaneously through addition to the C=C bonds. This account summarizes the recent advances in photoinduced radical cascade cyclization to the synthesis of cyclic compounds with C=C bonds working as the initial radical acceptors, and emphasis is put on the related reaction mechanisms.

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Carbon radical addition–cyclization reaction induced by ruthenium-photocatalyst under visible light irradiation

Cited by 25 publications

References 123 publications

Aqueous-Medium Carbon–Carbon Bond-Forming Radical Reactions Catalyzed by Excited Rhodamine B as a Metal-Free Organic Dye under Visible Light Irradiation

Aqueous-Medium Carbon–Carbon Bond-Forming Radical Reactions Catalyzed by Excited Rhodamine B as a Metal-Free Organic Dye under Visible Light Irradiation

Synthesis ofN-Containing Heterocyclic Compounds Using Visible-light Photoredox Catalysis

Synthesis of Cyclic Compounds via Photoinduced Radical Cyclization Cascade of C=C bonds

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