scholarly journals The involvement of the trisulfur radical anion in electron-catalyzed sulfur insertion reactions: facile synthesis of benzothiazine derivatives under transition metal-free conditions

2016 ◽  
Vol 7 (7) ◽  
pp. 4067-4072 ◽  
Author(s):  
Zheng-Yang Gu ◽  
Jia-Jia Cao ◽  
Shun-Yi Wang ◽  
Shun-Jun Ji
Keyword(s):  
Transition Metal ◽  
Radical Anion ◽  
Insertion Reaction ◽  
Insertion Reactions ◽  
Facile Synthesis ◽  
Metal Free ◽  
Practical Synthesis

An efficient and practical synthesis of benzothiazine by K2S initiated sulfur insertion reaction with enaminones via electron catalysis is developed.

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.

Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2, 4-dicarboxylates from methylene isocyanides and propiolaldehyde

2021 ◽  
Author(s):  
Xiaoli Huo ◽  
Xiaojuan Chen ◽  
Liya Yu ◽  
Chong Zhang ◽  
Linghui Zeng ◽  
...  
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Transformation Process ◽  
Facile Synthesis ◽  
Direct Transformation ◽  
Metal Free

A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2, 4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and...

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.

ChemInform Abstract: Transition-Metal-Free α-Arylation of β-Keto Amides via an Interrupted Insertion Reaction of Arynes.

ChemInform ◽  
2012 ◽  
Vol 43 (51) ◽  
pp. no-no
Author(s):  
Kishor Mohanan ◽  
Yoann Coquerel ◽  
Jean Rodriguez
Keyword(s):  
Transition Metal ◽  
Insertion Reaction ◽  
Metal Free

scholarly journals Reactivity Profiles of Diazo Amides, Esters, and Ketones in Transition-Metal-Free C–H Insertion Reactions

2019 ◽  
Vol 141 (8) ◽  
pp. 3558-3565 ◽  
Author(s):  
Sarah E. Cleary ◽  
Xin Li ◽  
Li-Cheng Yang ◽  
K. N. Houk ◽  
Xin Hong ◽  
...  
Keyword(s):  
Transition Metal ◽  
Insertion Reactions ◽  
Metal Free

Facile synthesis of 4-quinolone derivatives via one-pot cascade reaction under transition-metal-free conditions

2015 ◽  
Vol 56 (24) ◽  
pp. 3777-3781 ◽  
Author(s):  
Chao Huang ◽  
Jia-Hui Guo ◽  
Huang-Mei Fu ◽  
Ming-Long Yuan ◽  
Li-Juan Yang
Keyword(s):  
Transition Metal ◽  
Cascade Reaction ◽  
Facile Synthesis ◽  
One Pot ◽  
Metal Free ◽  
Quinolone Derivatives

Transition-metal free synthesis of N-Aryl carbazoles and their extended analogs

2021 ◽  
Author(s):  
Mikhail Feofanov ◽  
Vladimir Akhmetov ◽  
Ryo Takayama ◽  
Konstantin Amsharov
Keyword(s):  
Transition Metal ◽  
Facile Synthesis ◽  
Nucleophilic Substitutions ◽  
Metal Free ◽  
Electronic Transfer

Herein, we describe a facile synthesis of the N-arylated carbazoles via ladderization of fluorinated oligophenylenes. The reaction consists of two subsequent nucleophilic substitutions triggered by the electronic transfer from dimsyl...

Sign in / Sign up

Export Citation Format

Share Document