Chemoselective metal-free aerobic alcohol oxidation in lignin

A Rahimi, A Azarpira, H Kim, J Ralph…

Index: Rahimi, Alireza; Azarpira, Ali; Kim, Hoon; Ralph, John; Stahl, Shannon S. Journal of the American Chemical Society, 2013 , vol. 135, # 17 p. 6415 - 6418

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Citation Number: 156

Abstract

An efficient organocatalytic method for chemoselective aerobic oxidation of secondary benzylic alcohols within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol%; TEMPO= 2, 2, 6, 6-tetramethylpiperidine-N-oxyl) in combination with HNO3 and HCl (10 mol% each). Preliminary studies highlight the ...

 Related Synthetic Route
GUAIACYLGLYCEROL-BETA-GUAIACYL ETHER Structure

7382-59-4

GUAIACYLGLYCERO...

~42%

1-(4-Hydroxy-3-Methoxyphenyl)-3-hydroxy-2-(2-Methoxyphenoxy) propane-1-one Structure

22317-34-6

1-(4-Hydroxy-3-...

Vanillic acid Structure

121-34-6

Vanillic acid

Vanillin Structure

121-33-5

Vanillin

Ethyl (2-methoxyphenoxy)acetate Structure

13078-21-2

Ethyl (2-methox...

~%

1-(4-Hydroxy-3-Methoxyphenyl)-3-hydroxy-2-(2-Methoxyphenoxy) propane-1-one Structure

22317-34-6

1-(4-Hydroxy-3-...

1-(4-(benzyloxy)-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol Structure

22400-03-9

1-(4-(benzyloxy...

~%

1-(4-Hydroxy-3-Methoxyphenyl)-3-hydroxy-2-(2-Methoxyphenoxy) propane-1-one Structure

22317-34-6

1-(4-Hydroxy-3-...

4-(Benzyloxy)-3-methoxybenzaldehyde Structure

2426-87-1

4-(Benzyloxy)-3...

~%

1-(4-Hydroxy-3-Methoxyphenyl)-3-hydroxy-2-(2-Methoxyphenoxy) propane-1-one Structure

22317-34-6

1-(4-Hydroxy-3-...

Vanillic acid Structure

121-34-6

Vanillic acid

Guaiacol Structure

90-05-1

Guaiacol

~%

1-(4-Hydroxy-3-Methoxyphenyl)-3-hydroxy-2-(2-Methoxyphenoxy) propane-1-one Structure

22317-34-6

1-(4-Hydroxy-3-...

1-(3,4-dimethoxyphenyl)ethane-1,2-diol Structure

13443-56-6

1-(3,4-dimethox...

~6%

β-oxo-β-(3,4-dimethoxyphenyl)-ethanol Structure

37803-48-8

β-oxo-β-(3,4-di...

1,3-bis(3,4-dimethoxyphenyl)propane-1,3-dione Structure

52751-63-0

1,3-bis(3,4-dim...

2-Bromo-1-(3,4-dimethoxyphenyl)ethanone Structure

1835-02-5

2-Bromo-1-(3,4-...

~%

β-oxo-β-(3,4-dimethoxyphenyl)-ethanol Structure

37803-48-8

β-oxo-β-(3,4-di...

1,3-bis(3,4-dimethoxyphenyl)propane-1,3-dione Structure

52751-63-0

1,3-bis(3,4-dim...

3,4-Dimethoxyacetophenone Structure

1131-62-0

3,4-Dimethoxyac...

~%

β-oxo-β-(3,4-dimethoxyphenyl)-ethanol Structure

37803-48-8

β-oxo-β-(3,4-di...

1,3-bis(3,4-dimethoxyphenyl)propane-1,3-dione Structure

52751-63-0

1,3-bis(3,4-dim...

1-(3,4-Dimethoxyphenyl)-2-(2-methoxyphenoxy)ethanol Structure

17078-88-5

1-(3,4-Dimethox...

~89%

1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)ethanone Structure

22675-96-3

1-(3,4-dimethox...


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