Rapid Synthesis of Luotonin A Derivatives via Synergistic Visible-Light Photoredox and Acid Catalysis

2022 ◽  
Author(s):  
Feng Wu ◽  
Wuheng Dong ◽  
Sijie Fan ◽  
Yao Yuan ◽  
Caiyun Liang ◽  
...  
Keyword(s):  
Visible Light ◽  
Acid Catalysis ◽  
Rapid Synthesis ◽  
Luotonin A

An uncommon use of irradiated flavins: Brønsted acid catalysis

2020 ◽  
Vol 56 (42) ◽  
pp. 5661-5664
Author(s):  
Yukihiro Arakawa ◽  
Tomohiro Mihara ◽  
Hiroki Fujii ◽  
Keiji Minagawa ◽  
Yasushi Imada
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Acid Catalysis ◽  
Light Irradiation ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Mild Conditions ◽  
Brönsted Acid ◽  
Bronsted Acid Catalysis

Visible light irradiation to flavins in the presence of thiols and O2 provides Brønsted acidic species that can be used as efficient catalysts for thioacetalizations and for Mannich-type reactions under non-irradiation and mild conditions.

scholarly journals Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions

2017 ◽  
Vol 139 (27) ◽  
pp. 9120-9123 ◽  
Author(s):  
Xiaoqiang Huang ◽  
Taylor R. Quinn ◽  
Klaus Harms ◽  
Richard D. Webster ◽  
Lilu Zhang ◽  
...  
Keyword(s):  
Visible Light ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Lewis Acid Catalysis

Asymmetric alkylation of remote C(sp3)–H bonds by combining proton-coupled electron transfer with chiral Lewis acid catalysis

2017 ◽  
Vol 53 (64) ◽  
pp. 8964-8967 ◽  
Author(s):  
Wei Yuan ◽  
Zijun Zhou ◽  
Lei Gong ◽  
Eric Meggers
Keyword(s):  
Electron Transfer ◽  
Hydrogen Atom ◽  
Visible Light ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Hydrogen Atom Transfer ◽  
Lewis Acid Catalysis ◽  
Asymmetric Alkylation ◽  
Proton Coupled Electron Transfer ◽  
Chiral Lewis Acid

The catalytic asymmetric alkylation of the remote, unactivated δ-position of N-alkyl amides was enabled by the combination of visible-light-induced proton-coupled electron transfer, 1,5-hydrogen atom transfer, and chiral Lewis acid catalysis.

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
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Nitrogen Heterocycles ◽  
Light Irradiation ◽  
Radical Species ◽  
Efficient Procedure ◽  
Efficient Access ◽  
Luotonin A ◽  
Alkyl Iodides

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.

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