Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides

2013 ◽  
Vol 15 (11) ◽  
pp. 2664-2667 ◽  
Author(s):  
Yannan Cheng ◽  
Xiangyong Gu ◽  
Pixu Li
Keyword(s):  
Visible Light ◽  
Aryl Halides ◽  
Aromatic Substitution ◽  
Direct Arylation ◽  
Homolytic Aromatic Substitution

A new era for homolytic aromatic substitution: replacing Bu3SnH with efficient light-induced chain reactions

2016 ◽  
Vol 14 (16) ◽  
pp. 3849-3862 ◽  
Author(s):  
Michael Gurry ◽  
Fawaz Aldabbagh
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Aromatic Substitution ◽  
New Era ◽  
Chain Reactions ◽  
Radical Initiator ◽  
Aromatic Heterocycles ◽  
Recent Advances ◽  
Homolytic Aromatic Substitution

Recent advances such as visible-light photoredox catalysis have largely superseded radical initiator-mediated substitutions onto arenes and aromatic heterocycles.

scholarly journals Transition-metal-free α-arylation of oxindoles via visible-light-promoted electron transfer

2019 ◽  
Vol 10 (10) ◽  
pp. 3049-3053 ◽  
Author(s):  
Kangjiang Liang ◽  
Na Li ◽  
Yang Zhang ◽  
Tao Li ◽  
Chengfeng Xia
Keyword(s):  
Electron Transfer ◽  
Transition Metal ◽  
Transition Metals ◽  
Visible Light ◽  
Aryl Halides ◽  
Direct Arylation ◽  
Metal Free

An operationally simple photochemical strategy for the direct arylation of oxindoles with (hetero)aryl halides in the absence of both transition metals and photoredox catalysts has been developed.

Nucleophile/Electrophile Combinations in Aromatic Substitution: From Wheland to Wheland–Meisenheimer Intermediates Using Strongly Activated Arenes

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3347-3356 ◽  
Author(s):  
Gabriele Micheletti ◽  
Carla Boga
Keyword(s):  
Nitrogen Atom ◽  
Carbon Atom ◽  
Short Review ◽  
Alkyl Halides ◽  
Aryl Halides ◽  
Aromatic Substitution ◽  
Aromatic Carbon ◽  
Isolation And Characterization ◽  
Acyl Halides

This short review provides an overview on the interaction between 1,3,5-triaminobenzene derivatives and different kinds of electrophiles. Due to the ambident reactivity of these nucleophiles (i.e., at the nitrogen atom of the substituents and at the aromatic carbon atom) different compounds can be obtained. Particular attention is devoted to the detection, isolation, and characterization of covalent intermediates of aromatic substitution, starting from Wheland intermediates until the first detection and characterization of Wheland–Meisenheimer intermediates.1 Introduction2 Reactions between 1,3,5-Triaminobenzene Derivatives and Charged Electrophiles2.1 The Proton as an Electrophile2.2 Arenediazonium Salts as Electrophiles3 Reactions between 1,3,5-Triaminobenzene Derivatives and Neutral­ Electrophiles3.1 Alkyl Halides as Electrophiles3.2 Acyl Halides and Sulfonyl Chlorides as Electrophiles3.3 Aryl Halides and Heteroaryl Halides as Electrophiles3.4 Polynitroheteroaromatics as Electrophiles4 Conclusion

Iron-Catalyzed Direct Arylation of Unactivated Arenes with Aryl Halides

2010 ◽  
Vol 49 (11) ◽  
pp. 2004-2008 ◽  
Author(s):  
Wei Liu ◽  
Hao Cao ◽  
Aiwen Lei
Keyword(s):  
Aryl Halides ◽  
Direct Arylation

Solvent-free coupling of aryl halides with pyrroles applying visible-light photocatalysis

2017 ◽  
Vol 2 (4) ◽  
pp. 472-478 ◽  
Author(s):  
M. Obst ◽  
R. S. Shaikh ◽  
B. König
Keyword(s):  
Visible Light ◽  
Solvent Free ◽  
Aryl Halides ◽  
Visible Light Photocatalysis ◽  
Visible Light Driven

A novel reactor for solvent-free, visible-light-driven photocatalytic transformations was developed.

Copper ferrite catalyst for direct arylation of acidic C-H bonds in azoles with aryl aldehydes

2021 ◽  
Vol 10 (4) ◽  
pp. 64-68
Author(s):  
Cuong Vu Minh ◽  
Anh Nguyen Thai ◽  
Nam Phan Thanh Son ◽  
Tung Nguyen Thanh
Keyword(s):  
Functional Groups ◽  
Aryl Halides ◽  
Copper Ferrite ◽  
Coupling Reagents ◽  
Direct Arylation ◽  
Aryl Aldehydes ◽  
Benzaldehyde Derivatives

Coupling reagents toward direct arylation of C2-H bonds in aryl azoles are often limited to aryl halides. Herein we report a functionalization of the acidic sp2 C-H bonds in benzothiazoles with benzaldehyde derivatives. Reactions proceeded in the presence of commercially ready CuFe2O4 catalyst. Scope of functional groups included chloro, nitro, cyano, and ester groups.

Palladium chloride catalyzed photochemical Heck reaction

2013 ◽  
Vol 91 (5) ◽  
pp. 348-351 ◽  
Author(s):  
Suresh B. Waghmode ◽  
Sudhir S. Arbuj ◽  
Bina N. Wani ◽  
C.S. Gopinath
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Palladium Nanoparticles ◽  
Bond Formation ◽  
Aryl Halides ◽  
Palladium Chloride ◽  
Carbon Bond ◽  
Excellent Yield ◽  
Carbon Carbon Bond ◽  
Uv Visible

PdCl2 catalyzed carbon–carbon bond formation (Heck reaction) between substituted aryl halides and olefins was carried out without a ligand, under irradiation with UV–visible light. The results demonstrated that UV–visible light accelerated the rate of the reaction, leading to an excellent yield of corresponding products. The recovered palladium nanoparticles could be thermally recycled several times. PdCl2 gave excellent conversion up to the fifth addition of substrate.

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