Copper-Catalyzed Photoinduced Radical Domino Cyclization of Ynamides and Cyanamides: A Unified Entry to Rosettacin, Luotonin A, and Deoxyvasicinone

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 3022-3030 ◽  
Author(s):  
Gwilherm Evano ◽  
Hajar Baguia ◽  
Christopher Deldaele ◽  
Eugénie Romero ◽  
Bastien Michelet

A general and efficient procedure for the copper-catalyzed photoinduced radical domino cyclization of ynamides and cyanamides providing an efficient access to complex tri-, tetra- and pentacyclic nitrogen heterocycles is reported. Upon visible light irradiation in the presence of catalytic amounts of [(DPEphos)(bcp)Cu]PF6 and an amine, a range of unactivated aryl and alkyl iodides were shown to be smoothly transformed to the corresponding radical species, initiating the radical domino cyclization. This procedure provides a unified entry to rosettacin, luotonin A, and deoxyvasicinone that could be efficiently prepared in a limited number of steps.

2016 ◽  
Vol 14 (7) ◽  
pp. 2195-2199 ◽  
Author(s):  
Xiao-Jing Wei ◽  
Lin Wang ◽  
Shao-Fu Du ◽  
Li-Zhu Wu ◽  
Qiang Liu

An efficient access to 3,3-difluoro-2-oxindoles has been achieved via intramolecular aminocarbonyldifluoromethyl radical addition to arenes under visible-light irradiation.


2014 ◽  
Vol 50 (64) ◽  
pp. 8900-8903 ◽  
Author(s):  
Kazunari Nakajima ◽  
Mai Kitagawa ◽  
Yuya Ashida ◽  
Yoshihiro Miyake ◽  
Yoshiaki Nishibayashi

We have succeeded in the visible light-mediated synthetic use of α-aminoalkyl radicals derived from α-silyl secondary amines toward addition to α,β-unsaturated carbonyl compounds. The resulting γ-aminocarbonyl compounds are converted into γ-lactams and pyrroles in a one-pot process.


Author(s):  
Snehamol Mathew ◽  
Priyanka Ganguly ◽  
Stephen Rhatigan ◽  
Vignesh Kumaravel ◽  
Ciara Byrne ◽  
...  

Indoor surface contamination by microbes is a major public health concern. A damp environment is one potential sources for microbe proliferation. Smart photocatalytic coatings on building surfaces using semiconductors like titania (TiO<sub>2</sub>) can effectively curb this growing threat.<b> </b>Metal-doped titania in anatase phase has been proved as a promising candidate for energy and environmental applications. In this present work, the antimicrobial efficacy of copper (Cu) doped TiO<sub>2 </sub>(Cu-TiO<sub>2</sub>) was evaluated against <i>Escherichia coli</i> (Gram-negative) and <i>Staphylococcus aureus</i> (Gram-positive) under visible light irradiation. Doping of a minute fraction of Cu (0.5 mol %) in TiO<sub>2 </sub>was carried out <i>via</i> sol-gel technique. Cu-TiO<sub>2</sub> further calcined at various temperatures (in the range of 500 °C – 700 °C) to evaluate the thermal stability of TiO<sub>2</sub> anatase phase. The physico-chemical properties of the samples were characterised through X-ray diffraction (XRD), Raman spectroscopy, X-ray photo-electron spectroscopy (XPS) and UV-visible spectroscopy techniques. XRD results revealed that the anatase phase of TiO<sub>2</sub> was maintained well, up to 650 °C, by the Cu dopant. UV-DRS results suggested that the visible light absorption property of Cu-TiO<sub>2 </sub>was enhanced and the band gap is reduced to 2.8 eV. Density functional theory (DFT) studies emphasises the introduction of Cu<sup>+</sup> and Cu<sup>2+</sup> ions by replacing Ti<sup>4+</sup> ions in the TiO<sub>2</sub> lattice, creating oxygen vacancies. These further promoted the photocatalytic efficiency. A significantly high bacterial inactivation (99.9%) was attained in 30 mins of visible light irradiation by Cu-TiO<sub>2</sub>.


2020 ◽  
Vol 16 ◽  
Author(s):  
Yuxue Wei ◽  
Honglin Qin ◽  
Jinxin Deng ◽  
Xiaomeng Cheng ◽  
Mengdie Cai ◽  
...  

Introduction: Solar-driven photocatalytic hydrogen production from water splitting is one of the most promising solutions to satisfy the increasing demands of a rapidly developing society. CdS has emerged as a representative semiconductor photocatalyst due to its suitable band gap and band position. However, the poor stability and rapid charge recombination of CdS restrict its application for hydrogen production. The strategy of using a cocatalyst is typically recognized as an effective approach for improving the activity, stability, and selectivity of photocatalysts. In this review, recent developments in CdS cocatalysts for hydrogen production from water splitting under visible-light irradiation are summarized. In particular, the factors affecting the photocatalytic performance and new cocatalyst design, as well as the general classification of cocatalysts, are discussed, which includes a single cocatalyst containing noble-metal cocatalysts, non-noble metals, metal-complex cocatalysts, metal-free cocatalysts, and multi-cocatalysts. Finally, future opportunities and challenges with respect to the optimization and theoretical design of cocatalysts toward the CdS photocatalytic hydrogen evolution are described. Background: Photocatalytic hydrogen evolution from water splitting using photocatalyst semiconductors is one of the most promising solutions to satisfy the increasing demands of a rapidly developing society. CdS has emerged as a representative semiconductor photocatalyst due to its suitable band gap and band position. However, the poor stability and rapid charge recombination of CdS restrict its application for hydrogen production. The strategy of using a cocatalyst is typically recognized as an effective approach for improving the activity, stability, and selectivity of photocatalysts. Methods: This review summarizes the recent developments in CdS cocatalysts for hydrogen production from water splitting under visible-light irradiation. Results: Recent developments in CdS cocatalysts for hydrogen production from water splitting under visible-light irradiation are summarized. The factors affecting the photocatalytic performance and new cocatalyst design, as well as the general classification of cocatalysts, are discussed, which includes a single cocatalyst containing noble-metal cocatalysts, non-noble metals, metal-complex cocatalysts, metal-free cocatalysts, and multi-cocatalysts. Finally, future opportunities and challenges with respect to the optimization and theoretical design of cocatalysts toward the CdS photocatalytic hydrogen evolution are described. Conclusion: The state-of-the-art CdS for producing hydrogen from photocatalytic water splitting under visible light is discussed. The future opportunities and challenges with respect to the optimization and theoretical design of cocatalysts toward the CdS photocatalytic hydrogen evolution are also described.


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