Switchable Synthesis of α,α‐Dihalomethyl and α,α,α‐Trihalomethyl Ketones by Metal‐Free Decomposition of Enaminone C=C Double Bond

2020 ◽  
Vol 362 (4) ◽  
pp. 877-883 ◽  
Author(s):  
Yunyun Liu ◽  
Jin Xiong ◽  
Li Wei ◽  
Jie‐Ping Wan
Keyword(s):  
Double Bond ◽  
Metal Free ◽  
Free Decomposition

scholarly journals Chemoselective and metal-free reduction of α,β-unsaturated ketones by in situ produced benzeneselenol from O-(tert-butyl) Se-phenyl selenocarbonate

RSC Advances ◽  
2020 ◽  
Vol 10 (56) ◽  
pp. 33706-33717
Author(s):  
Andrea Temperini ◽  
Marco Ballarotto ◽  
Carlo Siciliano
Keyword(s):  
Double Bond ◽  
Hydrochloric Acid ◽  
Unsaturated Ketones ◽  
Metal Free ◽  
Tert Butyl ◽  
Carbon Double Bond

The carbon–carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol.

Metal-Free Addition of Boronic Acids to Silylnitronates

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 856-860
Author(s):  
Laurent El Kaïm ◽  
Mansour Dolé Kerim ◽  
Pakoupati Boyode ◽  
Julian Garrec
Keyword(s):  
Reaction Mechanism ◽  
Double Bond ◽  
Boronic Acids ◽  
Dft Study ◽  
Metal Free ◽  
Nitro Derivatives ◽  
Oxime Derivatives ◽  
Nitrogen Double Bond ◽  
First Time ◽  
Aryl Transfer

We report for the first time a metal-free addition of boronic acids to silylnitronates to afford oxime derivatives through aryl transfer on the carbon nitrogen double bond. A reaction mechanism has been proposed in relation with a DFT study on the key aryl transfer. This arylation process is effective for cycloalkenyl nitro derivatives leading to oximes that may be oxidatively converted into 3-arylisoxazole derivatives.

scholarly journals Novel Metal-Free Hydrogenation of the Carbon—Carbon Double Bond in Azulenoid Enones by Use of Cycloheptatriene and Protic Acid.

ChemInform ◽  
2006 ◽  
Vol 37 (46) ◽  
Author(s):  
Takatomo Kimura ◽  
Tohru Takahashi ◽  
Mitsuko Nishiura ◽  
Kimiaki Yamamura
Keyword(s):  
Double Bond ◽  
Metal Free ◽  
Carbon Double Bond

Metal-Free C=C Double Bond Cleavage on Enaminones for the Synthesis of α-Ketoamides by Free-Radical Aerobic Oxygenation

2019 ◽  
Vol 2019 (27) ◽  
pp. 4422-4425 ◽  
Author(s):  
Yiming Yang ◽  
Guofeng Zhong ◽  
Junfen Fan ◽  
Yunyun Liu
Keyword(s):  
Free Radical ◽  
Double Bond ◽  
Bond Cleavage ◽  
Metal Free

Cyclopropanation Reactions of Semi-stabilized and Non-stabilized Diazo Compounds

Synthesis ◽  
2019 ◽  
Vol 51 (21) ◽  
pp. 3947-3963 ◽  
Author(s):  
Emmanuelle M. D. Allouche ◽  
André B. Charette
Keyword(s):  
Cyclopropane Ring ◽  
Ring Closure ◽  
Diazo Compounds ◽  
Physiochemical Properties ◽  
Dipolar Cycloadditions ◽  
Metal Free ◽  
Subsequent Application ◽  
Effective Synthesis ◽  
Metal Catalyzed ◽  
Free Decomposition

The cyclopropane ring is present in a large number of bio­active molecules as its incorporation often greatly alters their physiochemical properties. The synthesis of such motif is therefore of interest. Diazo compounds are versatile and powerful reagents that can be used in a broad range of reactions, including cyclopropanation processes. However, in case of unstable diazo reagents such as the donor-substituted­ variants, their inherent toxicity and instability have hampered their effective synthesis and utilization. Herein, we report the recent­ advances devoted to the safe and facile production of these potentially hazardous species and their subsequent application in cyclopropanation reactions, allowing the synthesis of more complex cyclopropylated motifs.1 Introduction2 Halomethylmetal-Mediated Cyclopropanations3 Cyclopropanations through Metallic- or Free Carbenes3.1 Transition-Metal-Catalyzed Decomposition of Diazo Compounds3.2 Metal-Free Decomposition of Diazo Compounds4 Michael Induced Ring Closure (MIRC) Reactions4.1 Sulfur Ylides4.2 1,3-Dipolar Cycloadditions5 Conclusion

scholarly journals Vicinal difunctionalization of carbon–carbon double bond for the platform synthesis of trifluoroalkyl amines

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Ferenc Béke ◽  
Ádám Mészáros ◽  
Ágnes Tóth ◽  
Bence Béla Botlik ◽  
Zoltán Novák
Keyword(s):  
Double Bond ◽  
Transition Metal ◽  
High Efficiency ◽  
Chemical Nature ◽  
Synthetic Approach ◽  
Selective Synthesis ◽  
Reaction Conditions ◽  
Metal Free ◽  
Amine Compounds ◽  
Broad Scale

AbstractRegioselective vicinal diamination of carbon–carbon double bonds with two different amines is a synthetic challenge under transition metal-free conditions, especially for the synthesis of trifluoromethylated amines. However, the synthesis of ethylene diamines and fluorinated amine compounds is demanded, especially in the pharmaceutical sector. Herein, we demonstrate that the controllable double nucleophilic functionalization of an activated alkene synthon, originated from a trifluoropropenyliodonium salt with two distinct nucleophiles, enables the selective synthesis of trifluoromethylated ethylene amines and diamines on broad scale with high efficiency under mild reaction conditions. Considering the chemical nature of the reactants, our synthetic approach brings forth an efficient methodology and provides versatile access to highly fluorinated amines.

Potassium tert-Butoxide Mediated Reductive C–P Cross-Coupling of Arylvinyl Sulfides through C–S Bond Cleavage

Synlett ◽  
2020 ◽  
Author(s):  
Qingle Zeng ◽  
Jie Feng ◽  
Qiaoling Zhang ◽  
Fuhai Li ◽  
Lu Yang ◽  
...  
Keyword(s):  
Double Bond ◽  
Transition Metal ◽  
Bond Cleavage ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Phosphine Oxides ◽  
One Pot ◽  
Metal Free ◽  
Cross Coupling Reaction

AbstractA transition-metal-free t-BuOK-mediated reductive C–P cross-coupling reaction of arylvinyl sulfides with diarylphosphine oxides through C–S bond cleavage has been developed. This protocol not only permits the synthesis of diaryl(2-arylethyl)phosphine oxides, but also achieves an unprecedented construction of a C–P bond through C–S bond cleavage and reduction of a C–C double bond in one pot.

ChemInform Abstract: Metal Free Access to Amide Compounds via Peroxide-Mediated N=N Double Bond Cleavage of Azobenzenes.

ChemInform ◽  
2015 ◽  
Vol 46 (48) ◽  
pp. no-no
Author(s):  
Gang Hong ◽  
Dan Mao ◽  
Xiaoyan Zhu ◽  
Shengying Wu ◽  
Limin Wang
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Free Access ◽  
Metal Free

Metal-Free, NHPI Catalyzed Oxidative Cleavage of C–C Double Bond Using Molecular Oxygen as Oxidant

2012 ◽  
Vol 14 (16) ◽  
pp. 4158-4161 ◽  
Author(s):  
Riyuan Lin ◽  
Feng Chen ◽  
Ning Jiao
Keyword(s):  
Double Bond ◽  
Molecular Oxygen ◽  
Oxidative Cleavage ◽  
Metal Free

Metal free access to amide compounds via peroxide-mediated NN double bond cleavage of azobenzenes

2015 ◽  
Vol 2 (8) ◽  
pp. 985-989 ◽  
Author(s):  
Gang Hong ◽  
Dan Mao ◽  
Xiaoyan Zhu ◽  
Shengying Wu ◽  
Limin Wang
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Free Access ◽  
Metal Free ◽  
Direct Amidation

A direct amidation of aldehydes or benzylamines with azobenzenes through TBHP-mediated NN double bond cleavage of azobenzenes has been developed.

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