Photochemical Synthesis of Heterocycles: Merging Flow Processing and Metal-Catalyzed Visible Light Photoredox Transformations

2018 ◽  
pp. 103-132 ◽  
Author(s):  
Toma Glasnov
Keyword(s):  
Visible Light ◽  
Photochemical Synthesis ◽  
Metal Catalyzed

scholarly journals Copper’s rapid ascent in visible-light photoredox catalysis

Science ◽  
2019 ◽  
Vol 364 (6439) ◽  
pp. eaav9713 ◽  
Author(s):  
Asik Hossain ◽  
Aditya Bhattacharyya ◽  
Oliver Reiser
Keyword(s):  
Visible Light ◽  
Organic Dyes ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Photoredox Catalysis ◽  
Cross Coupling Reactions ◽  
Rapid Ascent ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

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.

Photochemical Synthesis of 1-Aminonorbornanes via Strain-Driven, Formal [3+2] Cycloadditions

2017 ◽  
Author(s):  
Daryl Staveness ◽  
Taylor Sodano ◽  
Corey Stephenson
Keyword(s):  
Drug Design ◽  
Visible Light ◽  
Continuous Flow ◽  
Chemical Space ◽  
Photochemical Synthesis ◽  
Design And Development ◽  
Simple Method ◽  
Modern Drug ◽  
Optically Pure ◽  
Unique Chemical

<p>This report describes a new route toward 1‑aminonorbornanes via strain-driven, visible light-mediated formal [3+2] cycloadditions with aminocyclopropanes. Lewis acidic salts (LiBF<sub>4</sub>, ZnCl<sub>2</sub>) were found to facilitate the oxidation of a variety of amine-containing heterocycles, and consequently, these additives led to improved conversion and isolated yields. This operationally-simple method tolerates a variety of functional handles (e.g. alcohols, protected amines), can generate optically-pure products through diastereoselective variations, and affords entry to unique chemical space through the diversity of accessible substitution patterns. Providing flexible access to 1-aminonorbornanes is expected to benefit modern drug design and development efforts seeking to incorporate more <i>sp<sup>3</sup></i>-rich motifs into lead scaffods. Further, gram-scale operation proceeds smoothly in continuous flow, suggesting that this chemistry can be readily translated beyond the academic- or discovery-scales.</p>

Facile photochemical synthesis of hierarchical cake-like ZnO/Ag composites with enhanced visible-light photocatalytic activities

2018 ◽  
Vol 219 ◽  
pp. 236-239 ◽  
Author(s):  
Miao Wang ◽  
Jinyu Xu ◽  
Tongming Sun ◽  
Yanfeng Tang ◽  
Guoqing Jiang ◽  
...  
Keyword(s):  
Visible Light ◽  
Photochemical Synthesis ◽  
Photocatalytic Activities ◽  
Visible Light Photocatalytic

Visible light photocatalysis as a greener approach to photochemical synthesis

2010 ◽  
Vol 2 (7) ◽  
pp. 527-532 ◽  
Author(s):  
Tehshik P. Yoon ◽  
Michael A. Ischay ◽  
Juana Du
Keyword(s):  
Visible Light ◽  
Photochemical Synthesis ◽  
Visible Light Photocatalysis

scholarly journals When metal-catalyzed C–H functionalization meets visible-light photocatalysis

2020 ◽  
Vol 16 ◽  
pp. 1754-1804 ◽  
Author(s):  
Lucas Guillemard ◽  
Joanna Wencel-Delord
Keyword(s):  
Visible Light ◽  
Organic Synthesis ◽  
Bond Activation ◽  
Visible Light Photocatalysis ◽  
Waste Generation ◽  
Complex Molecules ◽  
Environment Friendly ◽  
Mild Conditions ◽  
Radical Initiators ◽  
Metal Catalyzed

While aiming at sustainable organic synthesis, over the last decade particular attention has been focused on two modern fields, C–H bond activation, and visible-light-induced photocatalysis. Couplings through C–H bond activation involve the use of non-prefunctionalized substrates that are directly converted into more complex molecules, without the need of a previous functionalization, thus considerably reduce waste generation and a number of synthetic steps. In parallel, transformations involving photoredox catalysis promote radical reactions in the absence of radical initiators. They are conducted under particularly mild conditions while using the visible light as a cheap and economic energy source. In this way, these strategies follow the requirements of environment-friendly chemistry. Regarding intrinsic advantages as well as the complementary mode of action of the two catalytic transformations previously introduced, their merging in a synergistic dual catalytic system is extremely appealing. In that perspective, the scope of this review aims to present innovative reactions combining C–H activation and visible-light induced photocatalysis.

scholarly journals Arenophile-Mediated Photochemical Dearomatization of Nonactivated Arenes

2020 ◽  
Vol 74 (7) ◽  
pp. 577-583 ◽  
Author(s):  
Mikiko Okumura ◽  
David Sarlah
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Visible Light ◽  
Bioactive Compounds ◽  
Aromatic Compounds ◽  
Ring Opening ◽  
Organic Molecules ◽  
Building Blocks ◽  
Metal Catalyzed

Aromatic compounds are one of the most abundant classes of organic molecules and find utility as precursors for alicyclic hydrocarbon building blocks. While many established dearomatization reactions are exceptionally powerful, dearomatization with concurrent introduction of functionality, i.e. dearomative functionalization, is still a largely underdeveloped field. This review aims to provide an overview of our recent efforts and progress in the development of dearomative functionalization of simple and nonactivated arenes using arenophile-arene cycloaddition platform. These cycloadducts, formed via a visible-light-mediated [4+2]-photocycloaddition, can be elaborated in situ through olefin chemistry or transition-metal-catalyzed ring-opening with carbon-, nitrogen-, and oxygen-based nucleophiles, providing access to diverse structures with functional and stereochemical complexity. Moreover, the dearomatized products are amenable to further elaborations, which effectively install other functionalities onto the resulting alicyclic carbocycles. The utility of the arenophile-mediated dearomatization methods are also highlighted by the facile syntheses of natural products and bioactive compounds through novel disconnections.

Visible light-driven organic photochemical synthesis in China

2018 ◽  
Vol 62 (1) ◽  
pp. 24-57 ◽  
Author(s):  
Yiyun Chen ◽  
Liang-Qiu Lu ◽  
Da-Gang Yu ◽  
Cheng-Jian Zhu ◽  
Wen-Jing Xiao
Keyword(s):  
Visible Light ◽  
Photochemical Synthesis ◽  
Visible Light Driven

Photochemical synthesis of CdS-MIL-125(Ti) with enhanced visible light photocatalytic performance for the selective oxidation of benzyl alcohol to benzaldehyde

2017 ◽  
Vol 16 (6) ◽  
pp. 996-1002 ◽  
Author(s):  
Rui Zhang ◽  
Gang Li ◽  
Yue Zhang
Keyword(s):  
Visible Light ◽  
Benzyl Alcohol ◽  
Selective Oxidation ◽  
Photocatalytic Performance ◽  
Photochemical Synthesis ◽  
Oxidation Of Benzyl Alcohol ◽  
Photochemical Method ◽  
Visible Light Photocatalytic

CdS-MIL-125(Ti) was synthesized via a photochemical method and applied as a catalyst in the selective oxidation of benzyl alcohol to benzaldehyde.

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