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.

A metal-free route to alkynyl sulfones under photoinduced conditions with the insertion of sulfur dioxide

2020 ◽  
Vol 22 (6) ◽  
pp. 1906-1910 ◽  
Author(s):  
Xinxing Gong ◽  
Min Yang ◽  
Jin-Biao Liu ◽  
Fu-Sheng He ◽  
Xiaona Fan ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Metal Free

A metal-free route to alkynyl sulfones under photoinduced conditions is accomplished, starting from 4-alkyl Hantzsch esters, sulfur dioxide, and alkynyl bromides under visible light irradiation at room temperature.

Photocatalyst- and transition-metal-free α-allylation of N-aryl tetrahydroisoquinolines mediated by visible light

2020 ◽  
Vol 22 (3) ◽  
pp. 646-650 ◽  
Author(s):  
Zhuohua Li ◽  
Pengju Ma ◽  
Yongzhu Tan ◽  
Yufei Liu ◽  
Min Gao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Metal Free

A convenient and efficient α-allylation of N-aryl tetrahydroisoquinolines has been achieved. This transformation can be realized under only visible light irradiation without the aid of transition metals or photocatalysts.

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.

Metal free visible light driven oxidation of alcohols to carbonyl derivatives using 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst

RSC Advances ◽  
2015 ◽  
Vol 5 (102) ◽  
pp. 84328-84333 ◽  
Author(s):  
Suvendu Samanta ◽  
Papu Biswas
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Metal Free ◽  
Carbonyl Derivatives ◽  
Oxidation Of Alcohols ◽  
Visible Light Driven ◽  
High Yields

A metal-free transformation of alcohols to the corresponding carbonyls in high yields under visible-light irradiation has been achieved at room temperature using di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst.

Oxidative organophotoredox catalysis: a regioselective synthesis of 2-nitro substituted imidazopyridines and 3-substituted indoles, initiated by visible light

2016 ◽  
Vol 40 (11) ◽  
pp. 9694-9701 ◽  
Author(s):  
Snehlata Yadav ◽  
Madhulika Srivastava ◽  
Pratibha Rai ◽  
Bhartendu Pati Tripathi ◽  
Anu Mishra ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Bond Formation ◽  
Light Irradiation ◽  
Regioselective Synthesis ◽  
Metal Free

Intramolecular C–N heterocyclization and C–C bond formation under visible light irradiation at room temperature was accomplished with a metal-free photoredox catalyst.

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.

Photocatalytic transition-metal-free direct 3-alkylation of 2-aryl-2H-indazoles in dimethyl carbonate

2021 ◽  
Author(s):  
Chunhua Ma ◽  
Zhiwen Feng ◽  
Jing Li ◽  
Dandan Zhang ◽  
Wei Li ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Dimethyl Carbonate ◽  
Light Irradiation ◽  
Alkylation Reaction ◽  
Metal Free ◽  
Mild Conditions

A general transition-metal-free photocatalytic decarboxylative 3-alkylation reaction of 2-aryl-2H-indazoles was developed under visible-light irradiation under mild conditions.

Transition-metal-free, visible-light-mediated cyclization of o-azidoarylalkynes with aryl diazonium salts

2017 ◽  
Vol 41 (23) ◽  
pp. 14053-14056 ◽  
Author(s):  
Cheng Jin ◽  
Lianzheng Su ◽  
Daxi Ma ◽  
Mingrong Cheng
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Diazonium Salts ◽  
Metal Free

A visible-light promoted transformation of o-azidoarylalkynes and aryl diazonium salts for the synthesis of unsymmetrical 2,3-diaryl-substituted indoles under transition-metal-free conditions was described.

scholarly journals Visible-Light-Mediated Synthesis of Trifluoromethylthiolated Arenes

Synthesis ◽  
2018 ◽  
Vol 51 (14) ◽  
pp. 2865-2870 ◽  
Author(s):  
Clément Ghiazza ◽  
Cyrille Monnereau ◽  
Lhoussain Khrouz ◽  
Thierry Billard ◽  
Anis Tlili
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Reaction Conditions ◽  
Reaction Proceeds ◽  
Stable Reagent ◽  
Shelf Stable

The visible-light-mediated synthesis of trifluoromethylthiolated arenes in the presence of ruthenium-based photocatayst under mild reaction conditions is reported. The trifluoromethylthiolated arenes are obtained using the shelf-stable reagent trifluoromethyl toluenethiosulfonate at room temperature. The reaction proceeds selectively and does not require the presence of any additive. A mechanism is proposed based on the obtained results of EPR as well as luminescence

Sign in / Sign up

Export Citation Format

Share Document