Visible-Light Induced and Oxygen-Promoted Oxidative Cyclization of Aromatic Enamines for the Synthesis of Quinolines Derivatives

Xia, Xiao‐Feng; Zhang, Guowei; Wang, Dawei; Zhu, Su‐Li

doi:10.1021/acs.joc.7b01206

Cited by 56 publications

(26 citation statements)

References 43 publications

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“…Apart from the aforementioned studies, Cu(II) salts have been used in an intramolecular oxidative cyclization/oxygen insertion of aromatic enamines to furnish polysubstituted quinolines under mild reaction conditions (77). Bode and co-workers have used stoichiometric Cu(OTf ) 2 as the Lewis acid to lower oxidation potentials of demanding imine substrates that can then participate in photocatalytic syntheses of various aza-heterocycles by using the silicon amine protocol (SLAP) (78).…”

Section: Miscellaneous Examplesmentioning

confidence: 99%

Copper’s rapid ascent in visible-light photoredox catalysis

Hossain

Bhattacharyya

Reiser

2019

Science

518

302

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Visible-light photoredox catalysis offers a distinct activation mode complementary to thermal transition metal catalyzed reactions. The vast majority of photoredox processes capitalizes on precious metal ruthenium(II) or iridium(III) complexes that serve as single-electron reductants or oxidants in their photoexcited states. As a low-cost alternative, organic dyes are also frequently used but in general suffer from lower photostability. Copper-based photocatalysts are rapidly emerging, offering not only economic and ecological advantages but also otherwise inaccessible inner-sphere mechanisms, which have been successfully applied to challenging transformations. Moreover, the combination of conventional photocatalysts with copper(I) or copper(II) salts has emerged as an efficient dual catalytic system for cross-coupling reactions.

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Section: Miscellaneous Examplesmentioning

confidence: 99%

Copper’s rapid ascent in visible-light photoredox catalysis

Hossain

Bhattacharyya

Reiser

2019

Science

518

302

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“…Moreover, ketones instead of esters could be used. Additionally, one‐component photocatalytic cyclization was reported [121] …”

Section: Synthesis Of Quinolinesmentioning

confidence: 99%

2‐(Alkynyl)anilines and Derivatives — Versatile Reagents for Heterocyclic Synthesis

2022

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The transformations of 2‐alkynylanilines and their derivatives into heterocycles are surveyed. Depending on the substituents, catalysts, and reaction conditions, these substrates can be converted into indoles, quinolines, indolines, oxindoles, indoxiles, various polycyclic compounds, etc. This review aims to generalize and assess the patterns of reactivity, selectivity, and applicability of 2‐(alkynyl)anilines in heterocyclic chemistry. The review is divided into sections in accordance with the produced heterocycle. In summary, the title substrates are capable of cyclizing not only into five‐ and six‐membered rings, but also to produce seven‐ and even eight‐membered ring systems. The preparation of 2‐(alkynyl)anilines is not covered.

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“…Meanwhile, Zhou and co-workers reported a visible light mediated method for the synthesis of 3-acylindoles through the intramolecular cyclization of N,N-dialkylamines [111]. Similarly, Xia and co-workers introduced an enamine moiety into the substrates, which could be oxidized by a photocatalyst after the tautomerization to afford the Csp 3 radical, followed by further transformation to afford quinolones [112].…”

Section: Other Csp 3 Radical Reagentsmentioning

confidence: 99%

Visible light promoted difunctionalization reactions of alkynes

Ren

2019

Chinese Journal of Catalysis

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Visible light promoted difunctionalization of alkynes is reviewed. The difunctionalization reaction is achieved by different reagents. Radicals such as carbon (sp 3), carbon (sp 2), and other heteroatom (P, S, N, Se, O, and halide) radicals initiated by visible light can undergo radical addition to a carbon-carbon triple bond. Upon further transformation, the desired difunctionalized products are obtained. Some organometallic complexes can be activated by visible light; the difunctionalization of alkynes is catalyzed by these species. Other reagents like 1,3-dipole precursors could also react with alkynes to give difunctionalization products; here, the 1,3-dipole derivatives are obtained by visible light photocatalysis. So far, the strategy has been succeeded in the formation of CC bonds and C-X bonds. Several valuable chemical skeletons have been constructed under mild conditions. However, high regio-and stereoselectivities in some direct difunctionalization methodologies are yet to be achieved.

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Visible-Light Induced and Oxygen-Promoted Oxidative Cyclization of Aromatic Enamines for the Synthesis of Quinolines Derivatives

Cited by 56 publications

References 43 publications

Copper’s rapid ascent in visible-light photoredox catalysis

Copper’s rapid ascent in visible-light photoredox catalysis

2‐(Alkynyl)anilines and Derivatives — Versatile Reagents for Heterocyclic Synthesis

Visible light promoted difunctionalization reactions of alkynes

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