Visible light-induced tandem oxidative cyclization of 2-alkynylanilines with disulfides (diselenides) to 3-sulfenyl- and 3-selenylindoles under transition metal-free and photocatalyst-free conditions

2017 ◽  
Vol 4 (7) ◽  
pp. 1322-1330 ◽  
Author(s):  
Qing Shi ◽  
Pinhua Li ◽  
Yan Zhang ◽  
Lei Wang
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Oxidative Cyclization ◽  
Efficient Synthesis ◽  
Metal Free

A simple and efficient synthesis of 3-sulfenyl (3-selenyl) indoles via visible light-induced cyclization of 2-alkynylanilines with disulfides(diselenides) was developed under transition metal-free and photocatalyst-free conditions.

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.

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

Metal-free oxidative cyclization of trifluoroacetimidohydrazides with methylhetarenes: a facile access to 3-hetaryl-5-trifluoromethyl-1,2,4-triazoles

2021 ◽  
Author(s):  
Xiao-Feng Wu ◽  
Zhengkai Chen ◽  
Jiajun Zhang ◽  
Tian-Hui Xu
Keyword(s):  
Oxidative Cyclization ◽  
Efficient Synthesis ◽  
Metal Free

A metal-free oxidative cyclization of trifluoroacetimidohydrazides with methylhetarenes for the efficient synthesis of 3-hetaryl-5-trifluoromethyl-1,2,4-triazoles has been developed. Notable features of this protocol include readily accessible starting materials, a broad substrate...

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.

New Avenues in Radical Trifluoromethylselenylation with ­Trifluoromethyl Tolueneselenosulfonate

Synlett ◽  
2018 ◽  
Vol 30 (07) ◽  
pp. 777-782 ◽  
Author(s):  
Clément Ghiazza ◽  
Cyrille Monnereau ◽  
Lhoussain Khrouz ◽  
Maurice Médebielle ◽  
Thierry Billard ◽  
...  
Keyword(s):  
Cyclic Voltammetry ◽  
Transition Metal ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Diazonium Salts ◽  
Metal Free ◽  
Luminescence Measurement ◽  
Stable Reagent ◽  
Shelf Stable

We demonstrated that the shelf-stable reagent trifluoromethyl tolueneselenosulfonate can be involved in radical trifluoromethylselenylation. Upon visible-light irradiation, the homolysis of the reagent could take place at room temperature. This finding is explored for unprecedented C(sp2)–SeCF3 and C(sp3)–SeCF3 processes under transition-metal-free conditions. Mechanistic investigations, including cyclic voltammetry, luminescence measurement, and EPR studies, allowed the proposal of plausible mechanisms.1 Introduction.2 Reactivity of Reagent I with Diazonium Salts3 Reactivity of Reagent I with Alkenes and Alkynes4 Conclusion

scholarly journals Photocatalytic Synthesis of Tetra-Substituted Furans Promoted by Carbon Dioxide

2021 ◽  
Author(s):  
Ya-Ming Tian ◽  
Huaiju Wang ◽  
Ritu Ritu ◽  
Burkhard Koenig
Keyword(s):  
Carbon Dioxide ◽  
Transition Metal ◽  
Visible Light ◽  
Metal Free ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Visible Light Driven ◽  
Substituted Furans ◽  
Photocatalytic Synthesis

We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO2) atmosphere under mild conditions. It was found that...

Visible light-mediated transition metal-free esterification of amides with boronic acids

2020 ◽  
Vol 61 (43) ◽  
pp. 152444
Author(s):  
Hao Ding ◽  
Wan-Ying Qi ◽  
Jing-Song Zhen ◽  
Qiuping Ding ◽  
Yong Luo
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Boronic Acids ◽  
Metal Free

Metal-free photocatalytic trifluoromethylative pyridylation of unactivated alkenes

2018 ◽  
Vol 20 (22) ◽  
pp. 5209-5214 ◽  
Author(s):  
Yu-Tao He ◽  
Dahye Kang ◽  
Inwon Kim ◽  
Sungwoo Hong
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Photoredox Catalysis ◽  
Metal Free

An efficient, transition metal-free trifluoromethylative pyridylation of unactivated alkenes was achieved by visible-light-induced photoredox catalysis.

Transition metal-free, visible-light-mediated construction of α,β-diamino esters via decarboxylative radical addition at room temperature

2019 ◽  
Vol 6 (13) ◽  
pp. 2245-2249 ◽  
Author(s):  
Guibing Wu ◽  
Jingwen Wang ◽  
Chengyu Liu ◽  
Maolin Sun ◽  
Lei Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Radical Addition ◽  
Metal Free ◽  
Radical Coupling

A metal-free photoredox catalyzed decarboxylative radical coupling of free-carboxylic acids and glyoxylic oximes was developed to synthesize α,β-diamino acids.

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