scholarly journals Radical–Anion Coupling Through Reagent Design: Hydroxylation of Aryl Halides

2021 ◽  
Author(s):  
Andrew John Greener ◽  
Patrycja Ubysz ◽  
Will Owens-Ward ◽  
George Smith ◽  
Ivan Ocaña ◽  
...  
Keyword(s):  
Transition Metal ◽  
Radical Anion ◽  
Aryl Halides ◽  
Design And Development ◽  
Metal Free

The design and development of an oxime-based hydroxylation reagent, which can chemoselectively convert aryl halides (X = F, Cl, Br, I) into phenols under operationally simple, transition-metal-free conditions is described....

scholarly journals Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes

2021 ◽  
Author(s):  
Qing He ◽  
Wenli Wang ◽  
Yong Liang ◽  
Zunting Zhang ◽  
Stanislaw F. Wnuk
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Metal Free

Insertion Reaction of 2-Halo-N-allylanilines with K2S Involving Trisulfur Radical Anion: Synthesis of Benzothiazole Derivatives under Transition-Metal-Free Conditions

Synthesis ◽  
2020 ◽  
Author(s):  
Yan-Wei Zhao ◽  
Shun-Yi Wang ◽  
Xin-Yu Liu ◽  
Tian Jiang ◽  
Weidong Rao
Keyword(s):  
Transition Metal ◽  
Radical Anion ◽  
Radical Cyclization ◽  
Transition Metal Catalysis ◽  
Insertion Reaction ◽  
Metal Catalysis ◽  
Metal Free ◽  
Benzothiazole Derivatives

AbstractA synthesis of benzothiazole derivatives through the reaction of 2-halo-N-allylanilines with K2S in DMF is developed. The trisulfur radical anion S3·–, which is generated in situ from K2S in DMF, initiates the reaction without transition-metal catalysis or other additives. In addition, two C–S bonds are formed and heteroaromatization of benzothiazole is triggered by radical cyclization and H-shift.

scholarly journals SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Dong Zou ◽  
Lishe Gan ◽  
Fan Yang ◽  
Huan Wang ◽  
Youge Pu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Experimental Evidence ◽  
Radical Anion ◽  
Reaction Pathway ◽  
Cycloaddition Reaction ◽  
Electron Donors ◽  
Ring Closure ◽  
Computational Studies ◽  
Metal Free ◽  
Radical Coupling

AbstractThe use of nitroarenes as amino sources in synthesis is challenging. Herein is reported an unusual, straightforward, and transition metal-free method for the net [3 + 2]-cycloaddition reaction of 2-azaallyl anions with nitroarenes. The products of this reaction are diverse 2,5-dihydro-1,2,4-oxadiazoles (>40 examples, up to 95% yield). This method does not require an external reductant to reduce nitroarenes, nor does it employ nitrosoarenes, which are often used in N–O cycloadditions. Instead, it is proposed that the 2-azaallyl anions, which behave as super electron donors (SEDs), deliver an electron to the nitroarene to generate a nitroarene radical anion. A downstream 2-azaallyl radical coupling with a newly formed nitrosoarene is followed by ring closure to afford the observed products. This proposed reaction pathway is supported by computational studies and experimental evidence. Overall, this method uses readily available materials, is green, and exhibits a broad scope.

Transition metal-free and base-mediated transformation arylation of unactivated benzene with aryl halides in presence of N,N′-bis(salicylidene)ethylenediamine as organocatalyst

2018 ◽  
Vol 107 ◽  
pp. 87-91 ◽  
Author(s):  
Ehsan Ghonchepour ◽  
Mohammad Reza Islami ◽  
Hamid Mostafavi ◽  
Ahmad Momeni Tikdari ◽  
Iran Sheikhshoaie
Keyword(s):  
Transition Metal ◽  
Aryl Halides ◽  
Metal Free

Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes

2016 ◽  
Vol 81 (19) ◽  
pp. 9422-9427 ◽  
Author(s):  
Qing He ◽  
Liwen Wang ◽  
Yong Liang ◽  
Zunting Zhang ◽  
Stanislaw F. Wnuk
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Metal Free

Generation of Aryl Radicals from Aryl Halides: Rongalite-Promoted Transition-Metal-Free Arylation

2019 ◽  
Vol 84 (16) ◽  
pp. 9946-9956 ◽  
Author(s):  
Fazhi Yu ◽  
Runyu Mao ◽  
Mingcheng Yu ◽  
Xianfeng Gu ◽  
Yonghui Wang
Keyword(s):  
Transition Metal ◽  
Aryl Halides ◽  
Metal Free ◽  
Aryl Radicals
Sign in / Sign up

Export Citation Format

Share Document