Transition-Metal-Free Direct C–H Arylation of Quinoxalin-2(1H)-ones with Diaryliodonium Salts at Room Temperature

2017 ◽  
Vol 19 (7) ◽  
pp. 1530-1533 ◽  
Author(s):  
Kun Yin ◽  
Ronghua Zhang
Keyword(s):  
Transition Metal ◽  
Room Temperature ◽  
Metal Free ◽  
Diaryliodonium Salts

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 O-Arylation of Quinoxalin-2-ones with Diaryliodonium Salts

Heterocycles ◽  
2021 ◽  
Vol 103 (1) ◽  
pp. 502
Author(s):  
Masami Kuriyama ◽  
Osamu Onomura ◽  
Yuki Mochizuki ◽  
Tsubasa Miyagi ◽  
Kosuke Yamamoto ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Diaryliodonium Salts

Transition metal-free base-promoted arylation of sulfenate anions with diaryliodonium salts

2019 ◽  
Vol 6 (1) ◽  
pp. 32-35 ◽  
Author(s):  
Lei Wang ◽  
Mingjie Chen ◽  
Junliang Zhang
Keyword(s):  
Transition Metal ◽  
Free Base ◽  
Metal Free ◽  
Diaryliodonium Salts

A base-promoted formal arylation of general sulfenate anions with diaryliodonium salts under transition-metal-free conditions has been described.

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.

Intramolecular Hydroalkoxylation/Reduction and Hydroamination/Reduction of Unactivated Alkynes Using a Silane–Iodine Catalytic System

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4199-4204 ◽  
Author(s):  
Masatoshi Shibuya ◽  
Shoji Fujita ◽  
Yoshihiko Yamamoto
Keyword(s):  
Transition Metal ◽  
Catalytic System ◽  
Room Temperature ◽  
Metal Free

A transition-metal-free silane–iodine catalytic system comprising I2 and Et3SiH promotes intramolecular hydroalkoxylation/reduction and hydroamination/reduction of unactivated alkynes. This system allows the reaction to proceed at room temperature affording 2,4- and 2,5-disubstituted pyrrolidines as well as a 2,3-disubstituted tetrahydrofuran with high diastereoselectivity.

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.

Transition metal-free procedure for the synthesis of S-aryl dithiocarbamates using aryl diazonium fluoroborate in water at room temperature

2011 ◽  
Vol 13 (7) ◽  
pp. 1837 ◽  
Author(s):  
Tanmay Chatterjee ◽  
Sukalyan Bhadra ◽  
Brindaban C. Ranu
Keyword(s):  
Transition Metal ◽  
Room Temperature ◽  
Metal Free

Transition-Metal-Free N-Arylation of Carbazoles and C-Arylation of Tetrahydrocarbazoles by using Diaryliodonium Salts

2012 ◽  
Vol 1 (3) ◽  
pp. 218-221 ◽  
Author(s):  
Fenglou Guo ◽  
Limin Wang ◽  
Peiqi Wang ◽  
Jianjun Yu ◽  
Jianwei Han
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Diaryliodonium Salts

An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 727-734 ◽  
Author(s):  
Farnaz Jafarpour ◽  
Mohammad Asadpour ◽  
Meysam Azizzade ◽  
Mehran Ghasemi ◽  
Saideh Rajai-Daryasarei
Keyword(s):  
Transition Metal ◽  
Room Temperature ◽  
Bond Formation ◽  
Antidepressant Drug ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Potential Utility ◽  
Metal Free ◽  
Cross Coupling Reaction ◽  
High Yields

A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C–S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.

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