Visible-light-promoted selective C–H amination of heteroarenes with heteroaromatic amines under metal-free conditions

2017 ◽  
Vol 15 (45) ◽  
pp. 9590-9594 ◽  
Author(s):  
Supravat Samanta ◽  
Chitrakar Ravi ◽  
Sadu Nageswara Rao ◽  
Abhisek Joshi ◽  
Subbarayappa Adimurthy
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Room Temperature ◽  
Functional Group ◽  
Metal Free ◽  
High Degree

The regioselective C–H amination of quinoline amides (C5) and imidazopyridines (C3) under transition-metal-free conditions at room temperature with a high degree of functional group tolerance is reported.

Diiiodine/Potassium Persulfate Mediated Synthesis of 1,2,3-Thiadiazoles from N-Tosylhydrazones and a Thiocyanate Salt as a Sulfur Source under Transition-Metal-Free Conditions

Synlett ◽  
2021 ◽  
Author(s):  
Yadong Sun ◽  
Ablimit Abdukader ◽  
Yuhan Lu ◽  
Chenjiang Liu
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Room Temperature ◽  
Functional Group ◽  
Ammonium Thiocyanate ◽  
Potassium Persulfate ◽  
Sulfur Source ◽  
Coupling Reactions ◽  
Wide Scope ◽  
Metal Free

AbstractA highly efficient method for the synthesis of 1,2,3-thiadiazoles has been developed by utilizing readily available tosylhydrazones and ammonium thiocyanate with ecofriendly EtOH as the solvent at room temperature. The reaction shows a wide scope of substrates and good functional-group tolerance. This protocol can be scaled up to a gram level and can be applied to coupling reactions with 4-(4-bromophenyl)-1,2,3-thiadiazole as the substrate.

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

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.

Transition-metal-free, visible-light induced cyclization of arylsulfonyl chlorides with o-azidoarylalkynes: a regiospecific route to unsymmetrical 2,3-disubstituted indoles

2017 ◽  
Vol 53 (30) ◽  
pp. 4203-4206 ◽  
Author(s):  
Lijun Gu ◽  
Cheng Jin ◽  
Wei Wang ◽  
Yonghui He ◽  
Guangyu Yang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Room Temperature ◽  
Metal Free

A visible-light-catalyzed synthesis of unsymmetrical 2,3-diaryl-substituted indoles from arylsulfonyl chlorides and o-azidoarylalkynes at room temperature has been discovered.

Visible-Light-Driven Phosphonoalkylation of Alkenes

Synlett ◽  
2021 ◽  
Vol 32 (04) ◽  
pp. 378-382
Author(s):  
Yue-Ming Jiang ◽  
Jie Liu ◽  
Qiang Fu ◽  
Yu-Ming Yu ◽  
Da-Gang Yu
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Functional Group ◽  
Reaction Conditions ◽  
Metal Free ◽  
Alkyl Sulfonates ◽  
Visible Light Driven ◽  
High Yields

AbstractPhosphonylation of alkenes is important for the generation of valuable organophosphines. However, redox-neutral difunctionalization of alkenes with readily available H-P(O) compounds remains underdeveloped. Herein, we report the first visible-light-driven redox-neutral phosphonoalkylation of alkenes. A variety of organophosphorus-containing three-membered carbocyclic scaffolds are synthesized from alkene-bearing alkyl sulfonates with H-P(O) compounds. The transition-metal-free protocol displays good functional group tolerance, broad substrate scope, high yields, and mild reaction conditions.

scholarly journals A transition-metal-free & diazo-free styrene cyclopropanation

2019 ◽  
Vol 10 (40) ◽  
pp. 9374-9379 ◽  
Author(s):  
Ana G. Herraiz ◽  
Marcos G. Suero
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Functional Group ◽  
Metal Free

A visible-light-enabled, operationally simple cyclopropanation reaction of styrenes with excellent functional group tolerance and chemoselectivity via carbenoid-like radicals.

Transition-metal-free visible-light photoredox catalysis at room-temperature for decarboxylative fluorination of aliphatic carboxylic acids by organic dyes

2015 ◽  
Vol 51 (59) ◽  
pp. 11864-11867 ◽  
Author(s):  
Xinxin Wu ◽  
Chunna Meng ◽  
Xiaoqian Yuan ◽  
Xiaotong Jia ◽  
Xuhong Qian ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Organic Dyes ◽  
Photoredox Catalysis ◽  
Green Method ◽  
Metal Free ◽  
Aliphatic Carboxylic Acids

We report herein an efficient, general and green method for decarboxylative fluorination of aliphatic carboxylicacids.

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.

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.

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