Visible light promoted difunctionalization reactions of alkynes

Ren, Xuefei; Lu, Zhan

doi:10.1016/s1872-2067(19)63278-x

Cited by 71 publications

(23 citation statements)

References 191 publications

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“…Among others, we can name the reaction with azides that opened the way to click chemistry and transmetallation reactions, which are mechanisms exploited in several palladium-catalyzed processes. [156][157][158] In the field of alkyne reactivity in photocatalysis, 31,159,160 copper catalysis experienced a new wave of rising interest as the discovery of the novel reactivity features demonstrated its ability to catalyze reactions previously believed to be exclusive of noble metals. The report of a visible-light palladium-free copper-photocatalyzed Sonogashira reaction serves as a brilliant example.…”

Section: Alkynesmentioning

confidence: 99%

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

et al. 2022

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Section: Alkynesmentioning

confidence: 99%

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

et al. 2022

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“…Especially gold(I) has seen increasing attention for application in general catalysis, [51,67,68] visible-light mediated photoredox catalysis [52,[69][70][71][72] and anticancer applications. [73] Figure 3.6.…”

Section: Coordination Site and Metal Choicementioning

confidence: 99%

Heterobimetallic [2.2]Paracyclophane Complexes and Their Application in Photoredox Catalysis

Knoll¹

2020

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The most important goal of current chemistry research is to provide green and sustainable routes to compounds of interest. One way of addressing this is the use of abundant and inexpensive sources of energy to drive reactions, with the prime example being visible light in photoredox catalysis. One recent promising approach is the use of heterobimetallic catalysts where two metals work in a cooperative fashion to achieve the desired transformation. However, very little is known about the exact mechanism of cooperativity. This is due to a lack of heterobimetallic compounds that can be fine-tuned to obtain very specific answers regarding for example spatial design of the catalyst in question. In this work, [2.2]paracyclophane (PCP) is presented as a new platform on which to build distance-variable heterobimetallic complexes. PCP has been described as a "super-atom" molecule for its unique ability to hold up to 16 substituents in a precise spatial relationship to each other. By using PCP as a platform, it is shown that a range of defined heterobimetallic complexes can be designed and prepared (Figure 1.1). The methods necessary for the synthetic transformations are developed and investigated for their broader synthetic applicability. 51 (10-65%) Scheme 3.8 Nickel-catalyzed Kumada arylation of PCP bromide 51. Recently, the Kumada cross-coupling was used for the heteroarylation of electron-rich para-methoxy iodo-PCP 52 with 2-pyridyl magnesium bromide (53) to form biaryl 54 (Scheme 3.9) albeit in not satisfying yields. [88] Thus, a better synthetic strategy to access valuable biaryl 54 is necessary.

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“…High local concentrations, superior ability to harvest light, and synergy of multiple active sites in MOFs can enhance electrons, which plays a decisive role in the photocatalytic process. MOFs could provide an adjustable platform to assemble individual active components for harvesting solar energy based on photosensitizers, which can circumvent the disadvantages of commonly used homogeneous catalysts. , [Ru(bpy) 3 ] 2+ (bpy = 2,2′-bipyridine), a cationic complex, is a well-studied one-electron photoredox catalyst, , which plays a vital role in the fields of energy storage, hydrogen evolution from water, and oxygen evolution. − MOFs can be a perfect platform to install Ru(bpy) 3 2+ moieties to produce heterogeneous photocatalysts. Currently, most of the reported examples to load [Ru(bpy) 3 ] 2+ to MOFs were achieved via the postsynthetic modification method.…”

Section: Introductionmentioning

confidence: 99%

Template-Directed Fabrication of Highly Efficient Metal–Organic Framework Photocatalysts

Liu

Yang

et al. 2021

ACS Appl. Mater. Interfaces

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Photocatalysis is a powerful and versatile tool widely applied in the areas of synthesis chemistry. However, most of the photocatalysts currently used are homogeneous catalysts, which inevitably face issues such as product–catalyst separation and recyclability. Addressing this challenge, we utilized a homogeneous Ru photocatalyst as a structure-directing template to fabricate a series of isostructural photocatalyst-encapsulating metal–organic frameworks (photocatalyst@MOFs) with high porosity, robustness, and photocatalyst loading. The regular channels of MOF can disperse the encapsulated photocatalysts, promote the mass transfer of substrates and products, and provide an outstanding substrate confinement effect, thereby dramatically improving the catalytic activity and excellent recyclability toward valuable organic reactions. For instance, the MOF photocatalysts can catalyze the asymmetric Mannich reaction with ketones with high yields and excellent enantioselectivities (up to 99% ee), better than the reported photocatalyst. Significantly, this was the first case that heterogeneous MOF-based photocatalyst can catalyze the asymmetric Mannich reaction without cocatalysts under room temperature and visible light. This work not only explores an avenue to prepare heterogeneous photocatalysts but also broadens the application scope of MOF-based photocatalysts.

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Visible light promoted difunctionalization reactions of alkynes

Cited by 71 publications

References 191 publications

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

Heterobimetallic [2.2]Paracyclophane Complexes and Their Application in Photoredox Catalysis

Template-Directed Fabrication of Highly Efficient Metal–Organic Framework Photocatalysts

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