Organic letters

Cross dehydrogenative coupling via base-promoted homolytic aromatic substitution (BHAS): synthesis of fluorenones and xanthones

S Wertz, D Leifert, A Studer

Index: Wertz, Sebastian; Leifert, Dirk; Studer, Armido Organic Letters, 2013 , vol. 15, # 4 p. 928 - 931

Full Text: HTML

Citation Number: 71

Abstract

Cross dehydrogenative coupling reactions occurring via base-promoted homolytic aromatic substitutions (BHASs) are reported. Fluorenones and xanthones are readily prepared via CDC starting with readily available ortho-formyl biphenyls and ortho-formyl biphenylethers, respectively. The commercially available and cheap t BuOOH is used as an oxidant. Initiation of the radical chain reaction is best achieved with small amounts of FeCp2 (0.1 or ...

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4-fluorobiphenyl-2-carboxaldehyde Structure

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4-fluorobipheny...

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9H-Fluoren-9-one,2-fluoro- Structure

343-01-1

9H-Fluoren-9-on...

4,4'-difluoro-biphenyl-2-carbaldehyde Structure

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4,4'-difluoro-b...

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9H-Fluoren-9-one,2,7-difluoro- Structure

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9H-Fluoren-9-on...

4-Fluorobenzeneboronic acid Structure

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4-Fluorobenzene...

2-Bromo-5-fluorobenzaldehyde Structure

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2-Bromo-5-fluor...

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9H-Fluoren-9-one,2,7-difluoro- Structure

24313-53-9

9H-Fluoren-9-on...

N/A Structure

1422011-58-2

N/A

~65%

2,6-dimethoxyxanthen-9-one Structure

842-51-3

2,6-dimethoxyxa...

2-Fluoro-4-methoxybenzaldehyde Structure

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2-Fluoro-4-meth...

Mequinol Structure

150-76-5

Mequinol

~%

2,6-dimethoxyxanthen-9-one Structure

842-51-3

2,6-dimethoxyxa...

2-(4-methoxyphenyl)benzaldehyde Structure

16064-04-3

2-(4-methoxyphe...

~76%

9H-Fluoren-9-one,2-methoxy- Structure

3133-07-1

9H-Fluoren-9-on...

4-Methoxyphenylboronic acid Structure

5720-07-0

4-Methoxyphenyl...

2-Bromobenzaldehyde Structure

6630-33-7

2-Bromobenzaldehyde

~%

9H-Fluoren-9-one,2-methoxy- Structure

3133-07-1

9H-Fluoren-9-on...

4-Fluorobenzeneboronic acid Structure

1765-93-1

4-Fluorobenzene...

2-Bromobenzaldehyde Structure

6630-33-7

2-Bromobenzaldehyde

~95%

4'-Fluoro-[1,1'-biphenyl]-2-carbaldehyde Structure

192863-46-0

4'-Fluoro-[1,1'...

2-(3-methylphenyl)benzaldehyde Structure

216443-17-3

2-(3-methylphen...

~53%

1-methylfluoren-9-one Structure

5501-37-1

1-methylfluoren...

3-methylfluoren-9-one Structure

1705-89-1

3-methylfluoren...

m-Tolylboronic acid Structure

17933-03-8

m-Tolylboronic acid

2-Bromobenzaldehyde Structure

6630-33-7

2-Bromobenzaldehyde

~%

1-methylfluoren-9-one Structure

5501-37-1

1-methylfluoren...

3-methylfluoren-9-one Structure

1705-89-1

3-methylfluoren...

2-(1-Naphthalenyl)benzaldehyde Structure

142598-69-4

2-(1-Naphthalen...

~39%

BENZANTHRONE Structure

82-05-3

BENZANTHRONE

7H-Benzo[c]fluoren-7-one Structure

6051-98-5

7H-Benzo[c]fluo...

1-Naphthaleneboronic acid Structure

13922-41-3

1-Naphthalenebo...

2-Bromobenzaldehyde Structure

6630-33-7

2-Bromobenzaldehyde

~%

BENZANTHRONE Structure

82-05-3

BENZANTHRONE

7H-Benzo[c]fluoren-7-one Structure

6051-98-5

7H-Benzo[c]fluo...

2-(3,4-methylenedioxyphenoxy)benzaldehyde Structure

169805-31-6

2-(3,4-methylen...

~29%

[1,3]dioxolo[4,5-b]xanthen-10-one Structure

6720-25-8

[1,3]dioxolo[4,...

Sesamol Structure

533-31-3

Sesamol

2-Fluorobenzaldehyde Structure

446-52-6

2-Fluorobenzaldehyde

~%

[1,3]dioxolo[4,5-b]xanthen-10-one Structure

6720-25-8

[1,3]dioxolo[4,...

4-chloro-biphenyl-2-carbaldehyde Structure

1198208-10-4

4-chloro-biphen...

~63%

9H-Fluoren-9-one,2-chloro- Structure

3096-47-7

9H-Fluoren-9-on...

2-Bromo-5-chlorobenzaldehyde Structure

174265-12-4

2-Bromo-5-chlor...

Phenylboronic acid Structure

98-80-6

Phenylboronic acid

~%

9H-Fluoren-9-one,2-chloro- Structure

3096-47-7

9H-Fluoren-9-on...

4'-METHYL-[1,1'-BIPHENYL]-2-CARBALDEHYDE Structure

16191-28-9

4'-METHYL-[1,1'...

~66%

2-Methyl-9H-fluoren-9-one Structure

2840-51-9

2-Methyl-9H-flu...

2-Fluorobenzaldehyde Structure

446-52-6

2-Fluorobenzaldehyde

Mequinol Structure

150-76-5

Mequinol

~%

9H-XANTHEN-9-ONE, 2-METHOXY- Structure

1214-20-6

9H-XANTHEN-9-ON...

5-methylbiphenyl-2-carboxaldehyde Structure

934691-49-3

5-methylbipheny...

~72%

3-methylfluoren-9-one Structure

1705-89-1

3-methylfluoren...

2-(3-methylphenyl)benzaldehyde Structure

216443-17-3

2-(3-methylphen...

~24%

1-methylfluoren-9-one Structure

5501-37-1

1-methylfluoren...

3-methylfluoren-9-one Structure

1705-89-1

3-methylfluoren...

m-Tolylboronic acid Structure

17933-03-8

m-Tolylboronic acid

2-Bromobenzaldehyde Structure

6630-33-7

2-Bromobenzaldehyde

~%

1-methylfluoren-9-one Structure

5501-37-1

1-methylfluoren...

3-methylfluoren-9-one Structure

1705-89-1

3-methylfluoren...

p-Cresol Structure

106-44-5

p-Cresol

2-Fluorobenzaldehyde Structure

446-52-6

2-Fluorobenzaldehyde

~%

9H-Xanthen-9-one,2-methyl- Structure

6280-45-1

9H-Xanthen-9-on...

4'-Tert-butyl[1,1'-biphenyl]-2-carbaldehyde Structure

893738-46-0

4'-Tert-butyl[1...

~86%

2-tert-butylfluoren-9-one Structure

58775-11-4

2-tert-butylflu...

4-tert-Butylphenylboronic acid Structure

123324-71-0

4-tert-Butylphe...

~%

2-tert-butylfluoren-9-one Structure

58775-11-4

2-tert-butylflu...

p-Cresol Structure

106-44-5

p-Cresol

2-Fluorobenzaldehyde Structure

446-52-6

2-Fluorobenzaldehyde

~97%

2-(4-Methylphenoxy)benzaldehyde Structure

19434-35-6

2-(4-Methylphen...

m-Tolylboronic acid Structure

17933-03-8

m-Tolylboronic acid

2-Bromobenzaldehyde Structure

6630-33-7

2-Bromobenzaldehyde

~80%

2-(3-methylphenyl)benzaldehyde Structure

216443-17-3

2-(3-methylphen...


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