Transition Metal-Free Generation of N-Unsubstituted Imines from Benzyl Azides: Synthesis of N-Unsubstituted Homoallylic Amines

2015 ◽  
Vol 80 (7) ◽  
pp. 3656-3663 ◽  
Author(s):  
Suman Pramanik ◽  
Reddy Rajasekhar Reddy ◽  
Prasanta Ghorai
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Homoallylic Amines ◽  
Free Generation

Sonication and Microwave-Assisted Primary Amination of Potassium­ Aryltrifluoroborates and Phenylboronic Acids under Metal-Free Conditions

Synthesis ◽  
2017 ◽  
Vol 49 (11) ◽  
pp. 2555-2561 ◽  
Author(s):  
Dale Kuik ◽  
J. McCubbin ◽  
Geoffrey Tranmer
Keyword(s):  
Transition Metal ◽  
Reaction Times ◽  
Aqueous Sodium Hydroxide ◽  
Metal Free ◽  
Microwave Assisted ◽  
Free Generation ◽  
Phenylboronic Acids ◽  
Microwave Assisted Method ◽  
General Method ◽  
Electron Withdrawing Substituents

The transition-metal-free generation of a series of primary arylamines from potassium aryltrifluoroborates and phenylboronic acids­ is reported. The method uses a mild, inexpensive source of nitrogen (hydroxylamine-O-sulfonic acid) in cooperation with aqueous sodium hydroxide in acetonitrile. Both a sonication and a microwave-assisted method were developed, which are capable of converting ArBF3K functionalities into primary arylamines (ArNH2) in isolated yields of up to 78% (10 examples for each method). This report represents the first general method for the conversion of aryltrifluoroborates into primary arylamines under mild, transition-metal-free conditions in moderate to very good yields. The method is applicable to a wide array of substrates containing electron-donating, electron-neutral, or electron-withdrawing substituents. Both the sonication and microwave methods were also applied to the generation of anilines from phenylboronic acids in isolated yields of up to 96% (12 examples for each method) that were superior to existing room temperature methods in terms of yield, while also offering much shorter reaction times (15 min vs 16 h). In particular, the microwave method is the first to allow for the conversion of arylboronic acids containing strongly electron-withdrawing substituents into the corresponding anilines in good yields, along with electron-donating­ substituents in very good to excellent yields.

Transition metal-free generation of the acceptor/acceptor-carbene via α-elimination: synthesis of fluoroacetyl cyclopropanes

2016 ◽  
Vol 52 (41) ◽  
pp. 6817-6820 ◽  
Author(s):  
Yongdong Wang ◽  
Jing Han ◽  
Jie Chen ◽  
Weiguo Cao
Keyword(s):  
Transition Metal ◽  
Ring Expansion ◽  
Metal Free ◽  
Free Generation

An efficient transition metal-free approach for the generation of acceptor/acceptor-carbene followed by trapping with alkenes to provide fluoroacetyl cyclopropanes has been described. The resulting cyclopropanes could be further converted into the fluoromethyl dihydrofurans or fluorodihydropyrroles through ring-expansion processes.

Transition-metal-free catalytic hydroboration reduction of amides to amines

2020 ◽  
Vol 7 (21) ◽  
pp. 3515-3520
Author(s):  
Wubing Yao ◽  
Jiali Wang ◽  
Aiguo Zhong ◽  
Shiliang Wang ◽  
Yinlin Shao
Keyword(s):  
Transition Metal ◽  
Selective Catalytic Reduction ◽  
Catalytic Reduction ◽  
Value Added ◽  
Metal Free

The selective catalytic reduction of amides to value-added amine products is a desirable but challenging transformation.

Deaminative carbonylative thioesterification of activated alkylamines with thiophenols under transition-metal-free conditions

2021 ◽  
Author(s):  
Fengqian Zhao ◽  
Xiao-Feng Wu
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Metal Free

A transition-metal-free radical carbonylation of activated alkylamines with thiophenols has been successfully developed. Various thioesters were selectively produced with moderate to good yields.

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

Selective Oxidation of Alcohols Catalyzed by a Transition Metal-Free System of NHPI/DDQ/NaNO2

2011 ◽  
Vol 32 (1) ◽  
pp. 118-122 ◽  
Author(s):  
Lipeng ZHOU ◽  
Chaofeng ZHANG ◽  
Tao FANG ◽  
Bingbing ZHANG ◽  
Ying WANG ◽  
...  
Keyword(s):  
Transition Metal ◽  
Selective Oxidation ◽  
Free System ◽  
Metal Free ◽  
Oxidation Of Alcohols

Defect engineering and characterization of active sites for efficient electrocatalysis

Nanoscale ◽  
2021 ◽  
Vol 13 (6) ◽  
pp. 3327-3345
Author(s):  
Xuecheng Yan ◽  
Linzhou Zhuang ◽  
Zhonghua Zhu ◽  
Xiangdong Yao
Keyword(s):  
Transition Metal ◽  
Active Sites ◽  
Defect Engineering ◽  
Metal Free

This review highlights recent advancements in defect engineering and characterization of both metal-free carbons and transition metal-based electrocatalysts.

Transition metal free, green and facile halogenation of ketene dithioacetals using a KX–oxidant system

2021 ◽  
Author(s):  
Vishakha Rai ◽  
Ganesh Shivayogappa Sorabad ◽  
Mahagundappa Rachappa Maddani
Keyword(s):  
Transition Metal ◽  
Ambient Temperature ◽  
Metal Free ◽  
Ketene Dithioacetals ◽  
System P ◽  
Oxidative Halogenation ◽  
Potassium Halide

A facile oxidative halogenation of α-oxo ketene dithioacetals is achieved by using a potassium halide and an oxidant combination under transition metal free conditions at ambient temperature.

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