Visible-light-mediated radical insertion/cyclization cascade reaction: synthesis of phenanthridines and isoquinolines from isocyanides

Feng, Shangbiao; Li, Tao; Du, Chenglong; Chen, Peng; Song, Dengpeng; Li, Jinlai; Xie, Xingang; She, Xuegong

doi:10.1039/c7cc01813d

Cited by 47 publications

(21 citation statements)

References 63 publications

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“…The mechanistic studies revealed that this reaction goes through a visible light-mediated single electron transfer mechanism. Initially, the irradiation of [Ru- She and co-workers in 2017 disclosed [69] a simple and effective visible light-mediated route to prepare phenanthridine derivatives 188 a via single electron oxidation of ethers by using photoredox catalyst under the mild conditions. Different types of phenanthridine derivatives can be afforded with moderate to good yields by the photoredox catalyzed activation of the sp 3 CÀ H bond of ethers followed by the radical insertion/ cyclization cascade reaction (Scheme 78).…”

Section: Visible Light-mediated Ruthenium Catalyzed Reactionsmentioning

confidence: 99%

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

et al. 2021

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Phenanthridine derivatives are one of the most intensively studied families of biologically active compounds. There has been considerable scientific interest in the turn of this century in the synthesis of these N‐containing heterocycles as they are prevalent in many alkaloids and also possess striking biological activities including antibacterial, antifungal, antitumor activities. In this regard, a number of synthetic approaches toward the construction of phenanthridine moieties with various substituents, and to increase their yield have been developed by the synthetic organic community. Even though many researchers have developed various innovative methods for the synthesis of phenanthridine derivatives for the past few years, still there is substantial scope for the discovery of novel synthetic methods. In this review, the latest developments in the diverse synthetic strategies of phenanthridine derivatives in the presence and absence of metals were described. The present review also enlightens the use of different reagents, the diversity of the substrates identified, and the plausible mechanisms unravelled towards the construction of these biologically relevant scaffolds.

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Section: Visible Light-mediated Ruthenium Catalyzed Reactionsmentioning

confidence: 99%

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

et al. 2021

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“…Wide range of functional groups shows good tolerance under the optimized reaction conditions (Scheme 246). [38g] …”

Section: Synthesis Of Isoquinoline Derivativesmentioning

confidence: 99%

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

2020

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In the past decades, an enormous number of reports have been dedicated towards the synthesis of nitrogen containing heterocycles. This immense interest have emerged owing to their wide varieties of pharmacological activities. The present review focused on the synthesis of isoquinoline derivatives, a family of N-heterocycles showing a broad range of structural diversity, biological and pharmaceutical activities. The progress on their synthetic strategies using versatile approaches are discussed in details.

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“…The iminyl radical 127 undergoes CÀ C β-scission to afford cyanoalkyl radical 128, which adds to the isocyanide 1 In addition to Ir-mediated alkylated strategies, visible-light mediated Ru-catalysed single-electron oxidation of ethers was achieved by She and coworkers (Scheme 29). [68] It is a cascade reaction involving radical insertion followed by cyclization to afford phenanthridine and isoquinoline derivatives 134, 135. In this strategy, Ru(II) complex gets converted to its excited state upon visible light irradiation.…”

Section: Arylating Reagentsmentioning

confidence: 99%

Photocatalytical and Photochemical Generation of Imidoyl Radicals: Synthetic Applications

2020

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In the last few decades, the development in the field of radical chemistry has gained great attention. The majority of these radical strategies mainly depend on the in situ generation of reactive radical species by employing radical initiators such as oxidants and metal salts or methods such as photocatalysis and electrochemistry etc. This review covers the literature on the generation of imidoyl radicals using photoredox catalysis. In the majority of the reactions, the spontaneity of the underlying SET transitions is correlated by the compiled redox potential data of the reacting species for a better understanding of the readers. Besides, the applications of these reactive imidoyl radicals to access a variety of heterocycles such as benzothiazoles, indoles, quinoxalines, phenanthridines, isoquinolines, pyridines, and amides are also addressed.

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Visible-light-mediated radical insertion/cyclization cascade reaction: synthesis of phenanthridines and isoquinolines from isocyanides

Cited by 47 publications

References 63 publications

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

Photocatalytical and Photochemical Generation of Imidoyl Radicals: Synthetic Applications

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