Synthesis of 6-Thiocyanatophenanthridines by Visible-Light- and Air-Promoted Radical Thiocyanation of 2-Isocyanobiphenyls

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 176-180 ◽  
Author(s):  
Manjula Singh ◽  
Arvind Yadav ◽  
Lal Yadav ◽  
R. Singh
Keyword(s):  
Natural Resources ◽  
Visible Light ◽  
Room Temperature ◽  
Atmospheric Oxygen ◽  
Ammonium Thiocyanate ◽  
Radical Cyclization ◽  
Eosin Y ◽  
One Pot ◽  
Metal Free

A convenient, efficient, and metal-free synthesis of 6-thiocyanatophenanthridines by visible-light- and air-mediated, eosin Y-catalyzed, sequential radical cyclization and aromatization of 2-isocyanobiphenyls with ammonium thiocyanate is reported. Advantageously, the protocol utilizes inexpensive, clean, and sustainable natural resources such as visible light and atmospheric oxygen at room temperature in a one-pot procedure.

scholarly journals Eosin Y-catalyzed visible-light-mediated aerobic oxidative cyclization of N,N-dimethylanilines with maleimides

2015 ◽  
Vol 11 ◽  
pp. 425-430 ◽  
Author(s):  
Zhongwei Liang ◽  
Song Xu ◽  
Wenyan Tian ◽  
Ronghua Zhang
Keyword(s):  
Visible Light ◽  
Oxidative Cyclization ◽  
Eosin Y ◽  
Efficient Synthesis ◽  
One Pot ◽  
Bond Functionalization ◽  
Metal Free ◽  
Mild Conditions ◽  
Simple Strategy ◽  
Air Atmosphere

A novel and simple strategy for the efficient synthesis of the corresponding tetrahydroquinolines from N,N-dimethylanilines and maleimides using visible light in an air atmosphere in the presence of Eosin Y as a photocatalyst has been developed. The metal-free protocol involves aerobic oxidative cyclization via sp3 C–H bond functionalization process to afford good yields in a one-pot procedure under mild conditions.

Metal-Free Regioselective Alkylation of Imidazo[1,2-a]pyridines with N-Hydroxyphthalimide Esters under Organic Photoredox Catalysis

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 363-368 ◽  
Author(s):  
Can Jin ◽  
Bin Sun ◽  
Tengwei Xu ◽  
Liang Zhang ◽  
Rui Zhu ◽  
...  
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Eosin Y ◽  
Photoredox Catalysis ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Regioselective Alkylation ◽  
Decarboxylative Coupling ◽  
Aliphatic Carboxylic Acids

A visible-light-induced direct C–H alkylation of imidazo[1,2-a]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N-hydroxyphthalimide (NHP) esters as alkylation reagents. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) were tolerated in this protocol, giving the corresponding C-5-alkylated products in moderate to excellent yields. Mechanistic studies indicate that a radical decarboxylative coupling pathway was involved in this process.

One-pot Suzuki coupling of aromatic amines via visible light photocatalyzed metal free borylation using t-BuONO at room temperature

2016 ◽  
Vol 57 (14) ◽  
pp. 1551-1554 ◽  
Author(s):  
Sabir Ahammed ◽  
Shiny Nandi ◽  
Debasish Kundu ◽  
Brindaban C. Ranu
Keyword(s):  
Visible Light ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Suzuki Coupling ◽  
One Pot ◽  
Metal Free

Visible-light-enabled aerobic synthesis of benzoin bis-ethers from alkynes and alcohols

2018 ◽  
Vol 20 (24) ◽  
pp. 5479-5483 ◽  
Author(s):  
Wen-Long Lei ◽  
Biao Yang ◽  
Qing-Bao Zhang ◽  
Pan-Feng Yuan ◽  
Li-Zhu Wu ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis

The first visible-light enabled metal-free aerobic protocol for one-pot synthesis of benzoin bis-ethers from alkenes and alcohols has been developed at room temperature.

Metal-free, visible-light-promoted oxidative radical cyclization of N-biarylglycine esters: one-pot construction of phenanthridine-6-carboxylates in water

2019 ◽  
Vol 21 (16) ◽  
pp. 4406-4411 ◽  
Author(s):  
Palani Natarajan ◽  
Deachen Chuskit ◽  
Priya Priya
Keyword(s):  
Visible Light ◽  
Intramolecular Cyclization ◽  
Radical Cyclization ◽  
Cyclization Reaction ◽  
Ambient Conditions ◽  
One Pot ◽  
Light Blue ◽  
Metal Free ◽  
Air Atmosphere ◽  
Oxidative Radical Cyclization

A metal-free, visible-light (blue LED: hν = 425 ± 15 nm) photoredox-catalyzed intramolecular cyclization reaction of N-biarylglycine esters to phenanthridine-6-carboxylates in water under an open air atmosphere at ambient conditions has been developed.

Visible-Light-Promoted Difunctionalization of Olefins Leading to α-Thiocyanato Ketones

Synlett ◽  
2018 ◽  
Vol 29 (10) ◽  
pp. 1340-1345 ◽  
Author(s):  
Guangming Nan ◽  
Huilan Yue
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Ammonium Thiocyanate ◽  
Eosin Y

A simple and convenient visible-light-induced difunctionalization of alkenes with ammonium thiocyanate and dioxygen has been developed at room temperature. A series of α-thiocyanato ketones could be easily and efficiently obtained in moderate to good yields through the formation of C–S and C=O bonds simply by using nontoxic and inexpensive Na2-Eosin Y as a photocatalyst.

Highly chemoselective deoxygenation of N-heterocyclic N-oxides under transition metal-free conditions

2021 ◽  
Vol 19 (16) ◽  
pp. 3735-3742
Author(s):  
Se Hyun Kim ◽  
Ju Hyeon An ◽  
Jun Hee Lee
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Eosin Y ◽  
Metal Free ◽  
Simple Protocol

Here, we provide an operationally simple protocol for the highly chemoselective deoxygenation of various functionalized N-heterocyclic N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst.

Metal-free visible-light-induced aerobic oxidation of α-diazoesters leading to α-ketoesters in air

2021 ◽  
Author(s):  
Ruisheng Liu ◽  
Qishun Liu ◽  
Haoran Meng ◽  
Hongyu Ding ◽  
Jindong Hao ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Aerobic Oxidation ◽  
Metal Free

A metal-free and visible-light-induced strategy has been established for the construction of α-ketoesters via aerobic oxidation of α-diazoesters with dioxygen in air at room temperature.

Visible-light-promoted sulfonylation of thiols with aryldiazonium and sodium metabisulphite leading to unsymmetrical thiosulfonates

2021 ◽  
Author(s):  
Yu-Fen Lv ◽  
Jinyun Luo ◽  
Yuchuan Ma ◽  
Qi Dong ◽  
Lin He
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Metal Free ◽  
Sodium Metabisulphite ◽  
Three Component Reaction

A new visible-light-mediated protocol has been proposed for the synthesis of thiosulfonates via metal-free sulfonylation of thiols with aryldiazonium and sodium metabisulphite at room temperature. This mild three-component reaction, simply...

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