Tetrahedron

Synthesis of unsymmetrical biaryls by electroreductive cobalt-catalyzed cross-coupling of aryl halides

P Gomes, H Fillon, C Gosmini, E Labbé, J Périchon

Index: Gomes, Paulo; Fillon, Hyacinthe; Gosmini, Corinne; Labbe, Eric; Perichon, Jacques Tetrahedron, 2002 , vol. 58, # 42 p. 8417 - 8424

Full Text: HTML

Citation Number: 40

Abstract

The consumable anode process allows the electrochemical cross-coupling reaction between various functionalized aromatic halides (iodides, bromides and chlorides) in the presence of cobalt halides as catalyst in a mixed solvent acetonitrile/pyridine (9: 1). A great variety of unsymmetrical biaryls are obtained in moderate to excellent yields.

 Related Synthetic Route
4-Iodoanisole Structure

696-62-8

4-Iodoanisole

2-Bromobenzonitrile Structure

2042-37-7

2-Bromobenzonitrile

~81%

[1,1'-Biphenyl]-2,2'-dicarbonitrile Structure

4341-02-0

[1,1'-Biphenyl]...

4,4'-Dimethoxybiphenyl Structure

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4,4'-Dimethoxyb...

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Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

2-Bromobenzonitrile Structure

2042-37-7

2-Bromobenzonitrile

~0%

[1,1'-Biphenyl]-2,2'-dicarbonitrile Structure

4341-02-0

[1,1'-Biphenyl]...

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

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4-Iodoanisole Structure

696-62-8

4-Iodoanisole

2-Bromobenzonitrile Structure

2042-37-7

2-Bromobenzonitrile

~0%

[1,1'-Biphenyl]-2,2'-dicarbonitrile Structure

4341-02-0

[1,1'-Biphenyl]...

4,4'-Dimethoxybiphenyl Structure

2132-80-1

4,4'-Dimethoxyb...

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iodoanisole Structure

529-28-2

iodoanisole

Methyl 2-bromobenzoate Structure

610-94-6

Methyl 2-bromob...

~0%

Methyl benzoate Structure

93-58-3

Methyl benzoate

2,2'-dimethoxybiphenyl Structure

4877-93-4

2,2'-dimethoxyb...

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iodoanisole Structure

529-28-2

iodoanisole

Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

~0%

Ethyl benzoate Structure

93-89-0

Ethyl benzoate

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

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Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

4-Iodoanisole Structure

696-62-8

4-Iodoanisole

~0%

Ethyl benzoate Structure

93-89-0

Ethyl benzoate

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

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4-Bromoanisole Structure

104-92-7

4-Bromoanisole

Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

~0%

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

4,4'-Dimethoxybiphenyl Structure

2132-80-1

4,4'-Dimethoxyb...

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4-Iodoanisole Structure

696-62-8

4-Iodoanisole

2-Bromobenzonitrile Structure

2042-37-7

2-Bromobenzonitrile

~0%

[1,1'-Biphenyl]-2,2'-dicarbonitrile Structure

4341-02-0

[1,1'-Biphenyl]...

4,4'-Dimethoxybiphenyl Structure

2132-80-1

4,4'-Dimethoxyb...

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4-Iodoanisole Structure

696-62-8

4-Iodoanisole

Ethyl 4-iodobenzoate Structure

51934-41-9

Ethyl 4-iodobenzoate

~0%

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

4,4'-Dimethoxybiphenyl Structure

2132-80-1

4,4'-Dimethoxyb...

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4-Iodoanisole Structure

696-62-8

4-Iodoanisole

1-Ethyl-4-iodobenzene Structure

25309-64-2

1-Ethyl-4-iodob...

~0%

4,4'-Diethylbiphenyl Structure

13049-40-6

4,4'-Diethylbiphenyl

4,4'-Dimethoxybiphenyl Structure

2132-80-1

4,4'-Dimethoxyb...

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iodoanisole Structure

529-28-2

iodoanisole

Methyl 2-bromobenzoate Structure

610-94-6

Methyl 2-bromob...

~0%

Methyl benzoate Structure

93-58-3

Methyl benzoate

2,2'-dimethoxybiphenyl Structure

4877-93-4

2,2'-dimethoxyb...

Detail Learn More
iodoanisole Structure

529-28-2

iodoanisole

Methyl 2-bromobenzoate Structure

610-94-6

Methyl 2-bromob...

~90%

Methyl benzoate Structure

93-58-3

Methyl benzoate

2,2'-dimethoxybiphenyl Structure

4877-93-4

2,2'-dimethoxyb...

Detail Learn More
iodoanisole Structure

529-28-2

iodoanisole

Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

~87%

Ethyl benzoate Structure

93-89-0

Ethyl benzoate

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

Detail Learn More
iodoanisole Structure

529-28-2

iodoanisole

Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

~0%

Ethyl benzoate Structure

93-89-0

Ethyl benzoate

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

Detail Learn More
Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

4-Iodoanisole Structure

696-62-8

4-Iodoanisole

~0%

Ethyl benzoate Structure

93-89-0

Ethyl benzoate

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

Detail Learn More
3-Iodoanisole Structure

766-85-8

3-Iodoanisole

Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

~0%

Ethyl benzoate Structure

93-89-0

Ethyl benzoate

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

Detail Learn More
3-Bromothiophene Structure

872-31-1

3-Bromothiophene

1-(4-Bromophenyl)ethanone Structure

99-90-1

1-(4-Bromopheny...

~35%

4,4'-Diacetylbiphenyl Structure

787-69-9

4,4'-Diacetylbi...

1-(4-thiophen-3-ylphenyl)ethanone Structure

172035-84-6

1-(4-thiophen-3...

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3-Iodoanisole Structure

766-85-8

3-Iodoanisole

Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

~71%

Ethyl benzoate Structure

93-89-0

Ethyl benzoate

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

Detail Learn More
3-Iodoanisole Structure

766-85-8

3-Iodoanisole

Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

~0%

Ethyl benzoate Structure

93-89-0

Ethyl benzoate

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

Detail Learn More
4-Iodoanisole Structure

696-62-8

4-Iodoanisole

1-Ethyl-4-iodobenzene Structure

25309-64-2

1-Ethyl-4-iodob...

~0%

4,4'-Diethylbiphenyl Structure

13049-40-6

4,4'-Diethylbiphenyl

4,4'-Dimethoxybiphenyl Structure

2132-80-1

4,4'-Dimethoxyb...

Detail Learn More
3-Bromothiophene Structure

872-31-1

3-Bromothiophene

Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

~50%

ethyl 4-thiophen-3-ylbenzoate Structure

172035-83-5

ethyl 4-thiophe...

Learn More
3-Bromothiophene Structure

872-31-1

3-Bromothiophene

Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

~28%

Thiophene(SIV) Structure

188290-36-0

Thiophene(SIV)

ethyl 4-thiophen-3-ylbenzoate Structure

172035-83-5

ethyl 4-thiophe...

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Ethyl 4-bromobenzoate Structure

5798-75-4

Ethyl 4-bromobe...

2-Bromobenzonitrile Structure

2042-37-7

2-Bromobenzonitrile

~77%

[1,1'-Biphenyl]-2,2'-dicarbonitrile Structure

4341-02-0

[1,1'-Biphenyl]...

Diethyl 4,4'-biphenyldicarboxylate Structure

47230-38-6

Diethyl 4,4'-bi...

Detail Learn More

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