scholarly journals Unexpected Metal-Free Dehydrogenation of a β-Ketoester to a Phenol Using a Recyclable Oxoammonium Salt

Molbank ◽  
10.3390/m1180 ◽  
2021 ◽  
Vol 2021 (1) ◽  
pp. M1180
Author(s):  
Fabrizio Politano ◽  
William P. Brydon ◽  
Jyoti Nandi ◽  
Nicholas E. Leadbeater
Keyword(s):  
Previous Literature ◽  
Oxidative Functionalization ◽  
Dehydrogenation Reaction ◽  
Metal Free ◽  
Oxoammonium Salts ◽  
Oxoammonium Salt

The conversion of ethyl 2-oxocyclohexanecarboxylate to ethyl salicylate using an oxoammonium salt is reported. The dehydrogenation reaction is operationally simple and compares favorably with previous literature examples for the same transformation and expands the scope of oxoammonium salts as reagents for oxidative functionalization processes.

Metal-Free Synthesis of Pyrrolo[1,2-a]quinoxalines Mediated by TEMPO Oxoammonium Salts

Synthesis ◽  
2018 ◽  
Vol 50 (14) ◽  
pp. 2727-2740 ◽  
Author(s):  
Xiang-Ying Tang ◽  
Yue-fa Gong ◽  
Heng-rui Huo
Keyword(s):  
Carbonyl Compounds ◽  
One Pot ◽  
Metal Free ◽  
Oxoammonium Salts ◽  
One Pot Synthesis ◽  
Oxoammonium Salt

We herein describe a novel TEMPO oxoammonium salt initiated Pictet–Spengler reaction of imines, generated in situ from carbonyl compounds and pyrrole- or indole-containing substrates, to afford 4,5-dihydropyrrolo[1,2-a]quinoxalines or 5,6-dihydroindolo[1,2-a]quin­oxalines in good to excellent yields. Moreover, a one-pot synthesis of a biologically important quinoxaline is achieved via a cyclization–dehydrogenation process using one equivalent of the oxoammonium salt.

scholarly journals Metal Free Amino-Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt

2020 ◽  
Author(s):  
Alexandra Millimaci ◽  
Rowan Meador ◽  
Sara Dampf ◽  
John D. Chisholm
Keyword(s):  
Transition Metal ◽  
Solvent Effects ◽  
Free Amino ◽  
Oxidation Products ◽  
Direct Transition ◽  
Metal Free ◽  
Mild Conditions ◽  
Relative Stereochemistry ◽  
Oxoammonium Salt

<div> <div> <div> <p>4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate (Bobbitt’s salt) effectively activates electron rich alkenes and promotes the addition of anilines. This transformation provides a direct, transition metal free method for amino-oxidation of alkenes under mild conditions. The relative stereochemistry of the amino-oxidation is influenced by solvent effects, with both the syn and anti amino-oxidation products being accessible from identical starting materials. </p> </div> </div> </div>

Direct Oxidative Dearomatization of Indoles with Aromatic Ketones: Rapid Access to 2,2-Disubstituted Indolin-3-ones

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 763-768
Author(s):  
Jiarun Liu ◽  
Jiancheng Huang ◽  
Kuiyong Jia ◽  
Tianxing Du ◽  
Changyin Zhao ◽  
...  
Keyword(s):  
Oxidative Dearomatization ◽  
Aromatic Ketones ◽  
Metal Free ◽  
Rapid Access ◽  
Oxoammonium Salt

A metal-free oxidative dearomatization of indoles with aromatic ketones mediated by TEMPO oxoammonium salt is described. The dearomatization proceeds smoothly and displays a broad substrate scope with respect to both indoles and aromatic ketones in the presence of H2SO4, affording the corresponding 2,2-disubstituted indolin-3-ones in good yields.

Tandem Elimination-Oxidation of Tertiary Benzylic Alcohols with an Oxoammonium Salt

2021 ◽  
Author(s):  
Rowan Isabella Larkin Meador ◽  
Robert E Anderson ◽  
John D Chisholm
Keyword(s):  
Single Step ◽  
Allylic Oxidation ◽  
Benzylic Alcohols ◽  
Oxoammonium Salts ◽  
Oxoammonium Salt

Tertiary benzylic alcohols react with oxoammonium salts, undergoing a tandem elimination / allylic oxidation to provide an allylic ether product in a single step. This mode of reactivity provides a...

Nitrogen-doped graphene nanosheets as metal-free catalysts for dehydrogenation reaction of ethanol

RSC Advances ◽  
2016 ◽  
Vol 6 (16) ◽  
pp. 13450-13455 ◽  
Author(s):  
Shuangming Li ◽  
Wenping Wang ◽  
Xia Liu ◽  
Xiaoliang Zeng ◽  
Wenxiu Li ◽  
...  
Keyword(s):  
Graphene Nanosheets ◽  
Dehydrogenation Reaction ◽  
Nitrogen Doped ◽  
Metal Free ◽  
Nitrogen Doped Graphene ◽  
Doped Graphene ◽  
Dehydrogenation Of Ethanol

N-Doped graphene is used to catalyze the dehydrogenation of ethanol, wherein acetaldehyde is obtained with a hundred percent selectivity.

scholarly journals Metal Free Amino‐Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt

2020 ◽  
Author(s):  
Alexandra M. Millimaci ◽  
Rowan I. L. Meador ◽  
Sara J. Dampf ◽  
John D. Chisholm
Keyword(s):  
Free Amino ◽  
Metal Free ◽  
Oxoammonium Salt

scholarly journals Metal Free Amino-Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt

2020 ◽  
Author(s):  
Alexandra Millimaci ◽  
Rowan Meador ◽  
Sara Dampf ◽  
John D. Chisholm
Keyword(s):  
Transition Metal ◽  
Solvent Effects ◽  
Free Amino ◽  
Oxidation Products ◽  
Direct Transition ◽  
Metal Free ◽  
Mild Conditions ◽  
Relative Stereochemistry ◽  
Oxoammonium Salt

<div> <div> <div> <p>4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate (Bobbitt’s salt) effectively activates electron rich alkenes and promotes the addition of anilines. This transformation provides a direct, transition metal free method for amino-oxidation of alkenes under mild conditions. The relative stereochemistry of the amino-oxidation is influenced by solvent effects, with both the syn and anti amino-oxidation products being accessible from identical starting materials. </p> </div> </div> </div>

Sign in / Sign up

Export Citation Format

Share Document