Visible-Light-Promoted and One-Pot Synthesis of Phenanthridines and Quinolines from Aldehydes and <i>O</i>-Acyl Hydroxylamine

An, Xiao‐De; Yu, Shouyun

doi:10.1021/acs.orglett.5b01096

Cited by 139 publications

(40 citation statements)

References 72 publications

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“…193 Yu employed a catalytic amount of p -chlorobenzenesulfonic acid in the photocatalytic synthesis of azaarenes, presumably to facilitate formation of an acyl oxime precursor rather than to influence PET. 194 Qi and Zhang found that catalytic TsOH improved their synthesis of α-alkoxybenzamides. 195 König observed improved performance of photocatalytic amine deprotection at low pH, though the mechanistic basis of this effect was not determined.…”

Section: Photoinduced Electron Transfermentioning

confidence: 99%

Dual Catalysis Strategies in Photochemical Synthesis

2016

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The interaction between an electronically excited photocatalyst and an organic molecule can result in the genertion of a diverse array of reactive intermediates that can be manipulated in a variety of ways to result in synthetically useful bond constructions. This Review summarizes dual-catalyst strategies that have been applied to synthetic photochemistry. Mechanistically distinct modes of photocatalysis are discussed, including photoinduced electron transfer, hydrogen atom transfer, and energy transfer. We focus upon the cooperative interactions of photocatalysts with redox mediators, Lewis and Brønsted acids, organocatalysts, enzymes, and transition metal complexes.

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Section: Photoinduced Electron Transfermentioning

confidence: 99%

Dual Catalysis Strategies in Photochemical Synthesis

2016

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“…3‐(Trifluoromethyl)phenanthridine (3v): 23 Compound 3v was prepared according to the general experimental procedure as above, yield 0.210 g (85 %); white solid. 1 H NMR (500 MHz, CDCl 3 ): δ = 9.29 (d, J = 7.6 Hz, 1 H), 8.42–8.65 (m, 2 H), 7.96–8.14 (m, 2 H), 7.80–7.96 (m, 1 H), 7.65–7.80 (m, 1 H), 7.50 (s, 1 H) ppm.…”

Section: Methodsmentioning

confidence: 99%

Cascade C–C and C–N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinolines

Borah

Gogoi

2016

Eur J Org Chem

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A Pd‐catalyzed cascade process has been developed for the synthesis of quinoline and phenanthridine derivatives from various β‐chloro α,β‐unsaturated aldehydes and 2‐chloroaryl aldehydes, respectively, in good to high yields. The reaction proceeds through Pd‐catalyzed cascade carbon–carbon and carbon–nitrogen bond formation in a single reaction vessel. The requisite β‐chloro α,β‐unsaturated aldehydes were efficiently synthesized from their corresponding carbonyl compounds. The use of the ligand Sphos with Pd(OAc)2 is crucial for the successful implementation of the present cascade process. This synthetic protocol is also applied for the gram‐scale synthesis of a trispheridine alkaloid.

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“…Yu and An have developed an intermolecular one-pot C-N coupling of aldehydes and O-acyl hydroxylamines to give phenanthridines and quinolines (Scheme 61). 64 The in situ reaction between aldehydes and O-acyl hydroxylamines would give O-acyl oximes for the generation of iminyl radicals. Further cyclization would then take place and furnish the desired aza-arenes.…”

Section: Intermolecular Cyclizationmentioning

confidence: 99%

Recent Advances in Photocatalytic C–N Bond Coupling Reactions

Chan

Chow

2020

Synthesis

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Catalytic C–N bond formation is one of the major research topics in synthetic chemistry owing to the ubiquity of amino groups in natural products, synthetic intermediates and pharmaceutical agents. In parallel with well-established metal-catalyzed C–N bond coupling protocols, photocatalytic reactions have recently emerged as efficient and selective alternatives for the construction of C–N bonds. In this review, the progress made on photocatalytic C–N bond coupling reactions between 2012 and February 2020 is summarized.1 Introduction1.1 General Mechanisms for Photoredox Catalysis1.2 Pioneering Work2 C(sp2)–N Bond Formation2.1 Protocols Involving an External Oxidant2.2 Oxidant-Free Protocols3 C(sp3)–N Bond Formation3.1 Direct Radical–Radical Coupling3.2 Addition Reactions to Alkenes3.3 Reductive Amination of Carbonyl Compounds3.4 Decarboxylative Amination4 Cyclization Reactions4.1 C(sp2)–N Heterocycle Formation4.2 C(sp3)–N Heterocycle Formation5 Other Examples6 Conclusion and Outlook

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Visible-Light-Promoted and One-Pot Synthesis of Phenanthridines and Quinolines from Aldehydes and O-Acyl Hydroxylamine

Cited by 139 publications

References 72 publications

Dual Catalysis Strategies in Photochemical Synthesis

Dual Catalysis Strategies in Photochemical Synthesis

Cascade C–C and C–N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinolines

Recent Advances in Photocatalytic C–N Bond Coupling Reactions

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Visible-Light-Promoted and One-Pot Synthesis of Phenanthridines and Quinolines from Aldehydes and O-Acyl Hydroxylamine

Cited by 139 publications

References 72 publications

Dual Catalysis Strategies in Photochemical Synthesis

Dual Catalysis Strategies in Photochemical Synthesis

Cascade C–C and C–N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinol­ines

Recent Advances in Photocatalytic C–N Bond Coupling Reactions

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Cascade C–C and C–N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinolines