Visible‐Light‐Induced, Manganese‐Catalyzed Tandem Cyclization of 2‐Biphenyl Isocyanides with Cyclopropanols for the Synthesis of 6‐<i>β</i>‐Ketoalkyl Phenanthridines

Wang, Liping; Ding, Qiuping; Li, Xiaofang; Peng, Yiyuan

doi:10.1002/ajoc.201800733

Cited by 16 publications

(16 citation statements)

References 70 publications

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“…A similar photocatalyzed tandem insertion/cyclization approach based on isocyanides and amino acid/peptide-derived Katritzky salts as precursors of α-carbonyl radicals was likewise reported [50]. On the contrary, the Mn(acac) 3 photocatalyzed ring opening of cyclopropanol 6.2 gave an easy access to a β-carbonyl radical 6.5 • , which in turn added onto 2-biphenyl isocyanide 6.1 to give the corresponding 6-β-ketoalkyl phenanthridine 6.3 in a good yield (Scheme 6) [51].…”

Section: Synthesis Of Phenanthridines Via Photocatalyzed Intramoleculmentioning

confidence: 91%

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

Tito¹,

Abdulla²,

Ravelli³

et al. 2020

Beilstein J. Org. Chem.

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Section: Synthesis Of Phenanthridines Via Photocatalyzed Intramoleculmentioning

confidence: 91%

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

Tito¹,

Abdulla²,

Ravelli³

et al. 2020

Beilstein J. Org. Chem.

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“…The synthesis of phenanthridines employing a versatile free radical precursor, cyclopropanes, was reported by Y. Peng and co‐workers (Scheme 23). [66] They stated that visible light and Mn(acac) 3 photocatalyst was necessary to effect the tandem oxidative cyclization of 2‐biphenylisocyanide ( 88 ) and cyclopropanols ( 89 ). Further, an inert atmosphere was necessary for the efficient conversion of the reaction.…”

Section: Reaction Involving Photoredox Processmentioning

confidence: 99%

Visible‐Light‐Induced Manganese‐Catalyzed Reactions: Present Approach and Future Prospects

2021

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Visible‐light‐induced reactions have allowed researchers to attain unorthodox bond formation and elusive chemical processes under mild and inherently safe reaction conditions. However, these methods have relied heavily on Ru‐ and Ir‐based complexes or metal‐free chromophores. While the heavy transition metal complexes are limited by their high cost, toxicity, and adverse environmental effects. Metal‐free photo‐redox catalysts are restricted due to their poorer photo‐stability. In order to overcome these shortcomings, extensive research aimed towards utilizing 3d‐transition metals has come to the forefront. Manganese, in this regard, holds great promise as a versatile and economically sustainable 3d‐transition metal catalyst. Hence, it is not surprising that recent years have witnessed several advances in visible‐light‐mediated manganese catalysis in areas of organic, polymer, and materials chemistry. Manganese‐based heterogeneous systems have also been utilized to effect dimerization and oxygenation reactions showcasing the versatility of manganese. Moreover, manganese has enabled late‐stage functionalization of valuable medicinal compounds and natural products, which are all important from the viewpoint of medicinal and pharmaceutical chemistry. In the present review, comprehensive discussions on the advances, significance, approaches, and mechanistic aspects have been added for each photochemical reaction process. Further, the reaction scope, limitations, and future prospects of visible‐light‐induced manganese catalysis have also been reviewed.

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“…Ding and group reported [49] Mn(acac) 3 ‐catalyzed visible light‐mediated tandem oxidative cyclization of 2‐biphenyl isocyanides 8 with cyclopropanols 159 for the preparation of 6‐β‐keto alkyl phenanthridines 160 under external oxidant‐free conditions. This was a very useful synthetic method for preparing wide range of 6‐alkylated phenanthridines 160 via oxidative cyclization of 2‐biphenyl isocyanides 8 with different alkyl radical precursors with excellent to good yields (Scheme 50).…”

Section: Synthesis Of Phenanthridinesmentioning

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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Visible‐Light‐Induced, Manganese‐Catalyzed Tandem Cyclization of 2‐Biphenyl Isocyanides with Cyclopropanols for the Synthesis of 6‐β‐Ketoalkyl Phenanthridines

Cited by 16 publications

References 70 publications

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

Visible‐Light‐Induced Manganese‐Catalyzed Reactions: Present Approach and Future Prospects

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

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