Cascade Radical Reactions via α-(Arylsulfanyl)imidoyl Radicals:  Competitive [4 + 2] and [4 + 1] Radical Annulations of Alkynyl Isothiocyanates with Aryl Radicals§

2003 ◽  
Vol 68 (9) ◽  
pp. 3454-3464 ◽  
Author(s):  
Luisa Benati ◽  
Gianluca Calestani ◽  
Rino Leardini ◽  
Matteo Minozzi ◽  
Daniele Nanni ◽  
...  
Keyword(s):  
Radical Reactions ◽  
Aryl Radicals

σ-Bond initiated generation of aryl radicals from aryl diazonium salts

2020 ◽  
Vol 18 (9) ◽  
pp. 1812-1819 ◽  
Author(s):  
Elene Tatunashvili ◽  
Bun Chan ◽  
Philippe E. Nashar ◽  
Christopher S. P. McErlean
Keyword(s):  
Room Temperature ◽  
Radical Reactions ◽  
Diazonium Salts ◽  
Aryl Radicals

Hantzsch esters and oxygen convert diazonium salts into aryl radicals, enabling rapid radical reactions to be performed in open flasks at room temperature.

Direct C–H Functionalization of Heteroarenes via Redox-Neutral Radical Process: A Facile Route to C–C Bonds Formation

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3407-3421 ◽  
Author(s):  
Pin Gao ◽  
Yu-Rui Gu ◽  
Xin-Hua Duan
Keyword(s):  
Functional Group ◽  
Radical Reactions ◽  
Neutral Radical ◽  
Alkyl Radicals ◽  
Aryl Radicals ◽  
Mild Conditions ◽  
Wide Range ◽  
Carbon Radicals ◽  
Facile Route ◽  
Radical Functionalization

Aromatic heterocycles are an important class of compounds found in a wide range of natural products, pharmaceutically active molecules and organic materials. Recently, the direct radical functionalization of heteroaromatic C–H bonds has become an efficient and attractive method to access substituted heteroarenes. Especially, redox-neutral radical reactions have attracted much attention of chemists due to their potential advantages such as mild conditions, free of external oxidants, and good functional group tolerance. So far, a series of redox-neutral radical reactions have been developed. In this review, we mainly focus on the recent advance in direct redox-neutral radical C–H functionalization of heteroarenes. Herein, the direct C–H arylation, C–H alkylation, and C–H fluoroalkylation of heteroarenes are represented respectively, providing practical routes to C–C bond formation.1 Introduction2 C–H Arylation of Heteroarenes with Aryl Radicals3 C–H Alkylation of Heteroarenes with Alkyl Radicals4 C–H Fluoroalkylation of Heteroarenes with Fluorine-Containing Carbon Radicals5 Concluding Remarks

scholarly journals Aryl radical-mediated N-heterocyclic carbene catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yuki Matsuki ◽  
Nagisa Ohnishi ◽  
Yuki Kakeno ◽  
Shunsuke Takemoto ◽  
Takuya Ishii ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Single Electron ◽  
Radical Reactions ◽  
Single Electron Transfer ◽  
Aryl Radical ◽  
Aryl Iodide ◽  
Alkyl Radicals ◽  
Aryl Radicals ◽  
Electron Transfer Processes ◽  
Secondary Amides

AbstractThere have been significant advancements in radical reactions using organocatalysts in modern organic synthesis. Recently, NHC-catalyzed radical reactions initiated by single electron transfer processes have been actively studied. However, the reported examples have been limited to catalysis mediated by alkyl radicals. In this article, the NHC organocatalysis mediated by aryl radicals has been achieved. The enolate form of the Breslow intermediate derived from an aldehyde and thiazolium-type NHC in the presence of a base undergoes single electron transfer to an aryl iodide, providing an aryl radical. The catalytically generated aryl radical could be exploited as an arylating reagent for radical relay-type arylacylation of styrenes and as a hydrogen atom abstraction reagent for α-amino C(sp3)–H acylation of secondary amides.

Spatiotemporal Control of Amide Radicals During Photocatalysis

2020 ◽  
Author(s):  
Shogo Mori ◽  
Takahiro Aoki ◽  
Kaliyamoorthy Selvam ◽  
Shunichi Fukuzumi ◽  
Jieun Jung ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Nickel Complex ◽  
Nickel Complexes ◽  
Semiconductor Material ◽  
Radical Reactions ◽  
Substitution Reactions ◽  
Carbon Neutrality ◽  
Spatiotemporal Control ◽  
Scalable Production ◽  
Salt Waste

Despite the continuing popularity of radical reactions in organic synthesis, much remains to be explored in this area. Herein, we describe how spatiotemporal control can be exerted over the formation and reactivity of divergent exchangeable formamide radicals using nickel complexes with a semiconductor material (TiO<sub>2</sub>) under irradiation from near-UV–Vis light. Depending on the bipyridine ligand used and the quantity of the nickel complex that is hybridized on or nonhydridized over the TiO<sub>2</sub> surface, these radicals selectively undergo substitution reactions at the carbon center of carbon–bromine bonds that proceed via three different pathways. As the scalable production of formamides from CO<sub>2</sub> does not produce salt waste, these methods could add a new dimension to the search for carbon neutrality through the indirect incorporation of CO<sub>2</sub> into organic frameworks.

scholarly journals Reductive radical-polar crossover: traditional electrophiles in modern radical reactions

2019 ◽  
Vol 10 (36) ◽  
pp. 8285-8291 ◽  
Author(s):  
Lena Pitzer ◽  
J. Luca Schwarz ◽  
Frank Glorius
Keyword(s):  
Radical Reactions

The concept of reductive radical-polar crossover (RRPCO) reactions has recently emerged as a valuable and powerful tool to overcome limitations of both radical and traditional polar chemistry.

scholarly journals A Study on the Effects of 50 Hz Magnetic Fields on UV-induced Radical Reactions in Murine Fibroblasts

2010 ◽  
Vol 51 (5) ◽  
pp. 609-613 ◽  
Author(s):  
Ari MARKKANEN ◽  
Jonne NAARALA ◽  
Jukka JUUTILAINEN
Keyword(s):  
Magnetic Fields ◽  
Radical Reactions ◽  
Murine Fibroblasts
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