Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C–H oxygenation

C Huang, N Ghavtadze, B Chattopadhyay…

Index: Huang, Chunhui; Ghavtadze, Nugzar; Chattopadhyay, Buddhadeb; Gevorgyan, Vladimir Journal of the American Chemical Society, 2011 , vol. 133, # 44 p. 17630 - 17633

Full Text: HTML

Citation Number: 80

Abstract

A silanol-directed, Pd-catalyzed C–H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the ...

 Related Synthetic Route
ethyl 4-((di-tert-butyl(hydroxy)silyl)oxy)benzoate Structure

1344113-41-2

ethyl 4-((di-te...

~78%

Ethyl 3,4-dihydroxybenzoate Structure

3943-89-3

Ethyl 3,4-dihyd...

Ethylparaben Structure

120-47-8

Ethylparaben

~%

Ethyl 3,4-dihydroxybenzoate Structure

3943-89-3

Ethyl 3,4-dihyd...

3-Hydroxybenzaldehyde Structure

100-83-4

3-Hydroxybenzal...

~%

3,4-Diacetoxybenzaldehyde Structure

67727-64-4

3,4-Diacetoxybe...

N/A Structure

1344113-40-1

N/A

~87%

[1,1'-Biphenyl]-3,4-diol Structure

92-05-7

[1,1'-Biphenyl]...

3-Biphenylol Structure

580-51-8

3-Biphenylol

~%

[1,1'-Biphenyl]-3,4-diol Structure

92-05-7

[1,1'-Biphenyl]...

benzocatechol Structure

574-00-5

benzocatechol

Ethanoic anhydride Structure

108-24-7

Ethanoic anhydride

~%

1,2-Diacetoxynaphthalene Structure

6336-79-4

1,2-Diacetoxyna...

di-tert-butyl(4-methoxyphenoxy)silanol Structure

1315577-29-7

di-tert-butyl(4...

~%

acetic acid,4-methoxybenzene-1,2-diol Structure

82822-28-4

acetic acid,4-m...

di-tert-butyl((5,6,7,8-tetrahydronaphthalen-2-yl)oxy)silanol Structure

1315577-28-6

di-tert-butyl((...

~79%

5,6,7,8-tetrahydronaphthalene-2,3-diol Structure

3355-05-3

5,6,7,8-tetrahy...

5,6,7,8-Tetrahydro-2-naphthol Structure

1125-78-6

5,6,7,8-Tetrahy...

~%

5,6,7,8-tetrahydronaphthalene-2,3-diol Structure

3355-05-3

5,6,7,8-tetrahy...

N/A Structure

1315577-27-5

N/A

~67%

2,3-dihydro-1H-indene-5,6-diol Structure

3598-20-7

2,3-dihydro-1H-...

5-Indanol Structure

1470-94-6

5-Indanol

~%

2,3-dihydro-1H-indene-5,6-diol Structure

3598-20-7

2,3-dihydro-1H-...

2,2-di-tert-butylbenzo[d][1,3,2]dioxasilole Structure

1344113-53-6

2,2-di-tert-but...

~99%

1,2-Benzenediol Structure

120-80-9

1,2-Benzenediol

3-((di-tert-butyl(hydroxy)silyl)oxy)benzaldehyde Structure

1344113-46-7

3-((di-tert-but...

~%

3,4-Diacetoxybenzaldehyde Structure

67727-64-4

3,4-Diacetoxybe...

di-tert-butyl(m-tolyloxy)silanol Structure

1315577-23-1

di-tert-butyl(m...

~93%

4-methylcatechol Structure

452-86-8

4-methylcatechol

1-(3-((di-tert-butyl(hydroxy)silyl)oxy)phenyl)ethan-1-one Structure

1344113-47-8

1-(3-((di-tert-...

~%

(4-acetyl-2-acetyloxyphenyl) acetate Structure

72712-21-1

(4-acetyl-2-ace...

Di-tert-Butylsilane Structure

30736-07-3

Di-tert-Butylsilane

~90%

dibromo(ditert-butyl)silane Structure

94403-14-2

dibromo(ditert-...

3-ACETYLPHENOL Structure

121-71-1

3-ACETYLPHENOL

~%

(4-acetyl-2-acetyloxyphenyl) acetate Structure

72712-21-1

(4-acetyl-2-ace...

N/A Structure

1344113-44-5

N/A

~%

acetic acid,4-bromobenzene-1,2-diol Structure

66373-95-3

acetic acid,4-b...

4-Bromophenol Structure

106-41-2

4-Bromophenol

~%

acetic acid,4-bromobenzene-1,2-diol Structure

66373-95-3

acetic acid,4-b...

di-tert-butyl(3-iodophenoxy)silanol Structure

1344113-45-6

di-tert-butyl(3...

~%

4-IODO-1,2-BENZENEDIOL Structure

76149-14-9

4-IODO-1,2-BENZ...

3-Iodophenol Structure

626-02-8

3-Iodophenol

~%

4-IODO-1,2-BENZENEDIOL Structure

76149-14-9

4-IODO-1,2-BENZ...

di-tert-butyl(4-methoxyphenoxy)silanol Structure

1315577-29-7

di-tert-butyl(4...

~%

4-Methoxycatechol Structure

3934-97-2

4-Methoxycatechol


Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved