e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

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.

4-Iodoanisole Structure

2-Bromobenzonitrile Structure

2-Bromobenzonitrile

~81%

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

[1,1'-Biphenyl]...

4,4'-Dimethoxybiphenyl Structure

4,4'-Dimethoxyb...

Detail

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

2-Bromobenzonitrile Structure

2-Bromobenzonitrile

~0%

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

[1,1'-Biphenyl]...

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

Detail

4-Iodoanisole Structure

2-Bromobenzonitrile Structure

2-Bromobenzonitrile

~0%

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

[1,1'-Biphenyl]...

4,4'-Dimethoxybiphenyl Structure

4,4'-Dimethoxyb...

Detail

iodoanisole Structure

Methyl 2-bromobenzoate Structure

Methyl 2-bromob...

~0%

Methyl benzoate Structure

Methyl benzoate

2,2'-dimethoxybiphenyl Structure

2,2'-dimethoxyb...

Detail

iodoanisole Structure

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

~0%

Ethyl benzoate Structure

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

Detail

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

4-Iodoanisole Structure

~0%

Ethyl benzoate Structure

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

Detail

4-Bromoanisole Structure

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

~0%

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

4,4'-Dimethoxybiphenyl Structure

4,4'-Dimethoxyb...

Detail

4-Iodoanisole Structure

2-Bromobenzonitrile Structure

2-Bromobenzonitrile

~0%

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

[1,1'-Biphenyl]...

4,4'-Dimethoxybiphenyl Structure

4,4'-Dimethoxyb...

Detail

4-Iodoanisole Structure

Ethyl 4-iodobenzoate Structure

Ethyl 4-iodobenzoate

~0%

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

4,4'-Dimethoxybiphenyl Structure

4,4'-Dimethoxyb...

Detail

4-Iodoanisole Structure

1-Ethyl-4-iodobenzene Structure

1-Ethyl-4-iodob...

~0%

4,4'-Diethylbiphenyl Structure

4,4'-Diethylbiphenyl

4,4'-Dimethoxybiphenyl Structure

4,4'-Dimethoxyb...

Detail

iodoanisole Structure

Methyl 2-bromobenzoate Structure

Methyl 2-bromob...

~0%

Methyl benzoate Structure

Methyl benzoate

2,2'-dimethoxybiphenyl Structure

2,2'-dimethoxyb...

Detail

iodoanisole Structure

Methyl 2-bromobenzoate Structure

Methyl 2-bromob...

~90%

Methyl benzoate Structure

Methyl benzoate

2,2'-dimethoxybiphenyl Structure

2,2'-dimethoxyb...

Detail

iodoanisole Structure

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

~87%

Ethyl benzoate Structure

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

Detail

iodoanisole Structure

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

~0%

Ethyl benzoate Structure

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

Detail

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

4-Iodoanisole Structure

~0%

Ethyl benzoate Structure

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

Detail

3-Iodoanisole Structure

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

~0%

Ethyl benzoate Structure

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

Detail

3-Bromothiophene Structure

3-Bromothiophene

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

~35%

4,4'-Diacetylbiphenyl Structure

4,4'-Diacetylbi...

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

1-(4-thiophen-3...

3-Iodoanisole Structure

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

~71%

Ethyl benzoate Structure

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

Detail

3-Iodoanisole Structure

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

~0%

Ethyl benzoate Structure

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

Detail

4-Iodoanisole Structure

1-Ethyl-4-iodobenzene Structure

1-Ethyl-4-iodob...

~0%

4,4'-Diethylbiphenyl Structure

4,4'-Diethylbiphenyl

4,4'-Dimethoxybiphenyl Structure

4,4'-Dimethoxyb...

Detail

3-Bromothiophene Structure

3-Bromothiophene

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

~50%

ethyl 4-thiophen-3-ylbenzoate Structure

ethyl 4-thiophe...

3-Bromothiophene Structure

3-Bromothiophene

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

~28%

Thiophene(SIV) Structure

ethyl 4-thiophen-3-ylbenzoate Structure

ethyl 4-thiophe...

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

2-Bromobenzonitrile Structure

2-Bromobenzonitrile

~77%

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

[1,1'-Biphenyl]...

Diethyl 4,4'-biphenyldicarboxylate Structure

Diethyl 4,4'-bi...

Detail

Synthesis, characterization and X-ray structures of N-hetero...

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Convenient preparation of polyfunctional aryl magnesium reag...

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Microwave-assisted Negishi and Kumada cross-coupling reactio...

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