Transition-Metal-Free Aerobic Oxidative Cleavage of CC Bonds in α-Hydroxy Ketones and Mechanistic Insight to the Reaction Pathway

2012 ◽  
Vol 51 (50) ◽  
pp. 12570-12574 ◽  
Author(s):  
Hui Liu ◽  
Chao Dong ◽  
Zeguang Zhang ◽  
Peiyu Wu ◽  
Xuefeng Jiang
Keyword(s):  
Transition Metal ◽  
Reaction Pathway ◽  
Oxidative Cleavage ◽  
Metal Free ◽  
Mechanistic Insight ◽  
Hydroxy Ketones

Transition-Metal-Free Aerobic Oxidative Cleavage of CC Bonds in α-Hydroxy Ketones and Mechanistic Insight to the Reaction Pathway

2012 ◽  
Vol 124 (50) ◽  
pp. 12738-12742 ◽  
Author(s):  
Hui Liu ◽  
Chao Dong ◽  
Zeguang Zhang ◽  
Peiyu Wu ◽  
Xuefeng Jiang
Keyword(s):  
Transition Metal ◽  
Reaction Pathway ◽  
Oxidative Cleavage ◽  
Metal Free ◽  
Mechanistic Insight ◽  
Hydroxy Ketones

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 aerobic oxidative cleavage of the C–N bonds of α-amino esters

2019 ◽  
Vol 6 (23) ◽  
pp. 3854-3858
Author(s):  
Shenpeng Tan ◽  
Feng Li ◽  
Soojun Park ◽  
Sanghee Kim
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Metal Catalysts ◽  
Oxidative Cleavage ◽  
Amino Acid Derivatives ◽  
Metal Free ◽  
Amino Esters

A base-mediated aerobic oxidative cleavage of α-amino esters involving a hydroperoxide intermediate was reported, which represents the first example of the cleavage of the α-C–N bonds of amino acid derivatives without the aid of metal catalysts.

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