Transition-Metal-Free Synthesis of Carbonyl-Containing Oxindoles from N-Arylacrylamides and α-Diketones via TBHP- or Oxone-Mediated Oxidative Cleavage of C(sp2)–C(sp2) Bonds

2015 ◽  
Vol 80 (21) ◽  
pp. 10777-10786 ◽  
Author(s):  
Ming-Zhong Zhang ◽  
Peng-Yi Ji ◽  
Yu-Feng Liu ◽  
Can-Cheng Guo
Keyword(s):  
Transition Metal ◽  
Oxidative Cleavage ◽  
Metal Free

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.

scholarly journals Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone®

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2378
Author(s):  
Paola S. Hellwig ◽  
Jonatan S. Guedes ◽  
Angelita M. Barcellos ◽  
Gelson Perin ◽  
Eder J. Lenardão
Keyword(s):  
Transition Metal ◽  
Oxidative Cleavage ◽  
Aliphatic Alcohols ◽  
Electrophilic Cyclization ◽  
Metal Free ◽  
Selective Formation

We describe herein an alternative transition-metal-free procedure to access 3,4-bis(butylselanyl)selenophenes and the so far unprecedented 3-(butylselanyl)-4-alkoxyselenophenes. The protocol involves the 5-endo-dig electrophilic cyclization of 1,3-diynes promoted by electrophilic organoselenium species, generated in situ through the oxidative cleavage of the Se-Se bond of dibutyl diselenide using Oxone® as a green oxidant. The selective formation of the title products was achieved by controlling the solvent identity and the amount of dibutyl diselenide. By using 4.0 equiv of dibutyl diselenide and acetonitrile as solvent at 80 °C, four examples of 3,4-bis(butylselanyl)selenophenes were obtained in moderate to good yields (40–78%). When 3.0 equiv of dibutyl diselenide were used, in the presence of aliphatic alcohols as solvent/nucleophiles under reflux, 10 3-(butylselanyl)-4-alkoxyselenophenes were selectively obtained in low to good yields (15–80%).

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

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.

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