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

Palladium??Catalysed Direct C??H Activation/Arylation of Heteroaromatics: An Environmentally Attractive Access to Bi??or Polydentate Ligands

F Derridj, AL Gottumukkala, S Djebbar…

Index: Derridj, Fazia; Gottumukkala, Aditya L.; Djebbar, Safia; Doucet, Henri European Journal of Inorganic Chemistry, 2008 , # 16 p. 2550 - 2559

Full Text: HTML

Citation Number: 38

Abstract

Abstract Bi-or polydentate ligands based on heterocycles can be easily prepared by palladium-catalysed C–H bond activation of heteroaromatics followed by heteroarylation with heteroaryl bromides. A variety of heteroaromatics such as furans, thiophenes, pyridines, thiazoles or oxazole derivatives have been employed and moderate to good yields were generally obtained using the air-stable complex [PdCl (dppb)(C 3 H 5)] as catalyst. A ...

2-Bromo-6-methylpyridine Structure

2-Bromo-6-methy...

Benzo[d]thiazole Structure

Benzo[d]thiazole

~55%

2-(6-methylpyridin-2-yl)-1,3-benzothiazole Structure

2-(6-methylpyri...

6,6'-Dimethyl-2,2'-bipyridine Structure

6,6'-Dimethyl-2...

methylthiol Structure

5-Bromo-2-thiophenecarbaldehyde Structure

5-Bromo-2-thiop...

~63%

[2,2’]bithiophenyl-5,5'-dicarbaldehyde Structure

[2,2’]bithiophe...

5-(5-methylthiophen-2-yl)thiophene-2-carbaldehyde Structure

5-(5-methylthio...

2-Bromo-6-methylpyridine Structure

2-Bromo-6-methy...

1-Methylbenzimidazole Structure

1-Methylbenzimi...

~30%

6,6'-Dimethyl-2,2'-bipyridine Structure

6,6'-Dimethyl-2...

1-methyl-2-(6-methylpyridin-2-yl)benzimidazole Structure

1-methyl-2-(6-m...

2-Bromo-5-methylthiophene Structure

2-Bromo-5-methy...

Benzoxazole Structure

~0%

2,2'-Bithiophene,5,5'-dimethyl- Structure

2,2'-Bithiophen...

2-(5-methylthiophen-2-yl)benzoxazole Structure

2-(5-methylthio...

2-Bromo-5-methylthiophene Structure

2-Bromo-5-methy...

2-propyl thiazole Structure

2-propyl thiazole

~0%

2,2'-Bithiophene,5,5'-dimethyl- Structure

2,2'-Bithiophen...

5-(5-methylthiophen-2-yl)-2-propylthiazole Structure

5-(5-methylthio...

2-Chlorothiophene Structure

2-Chlorothiophene

2-Bromo-5-methylthiophene Structure

2-Bromo-5-methy...

~0%

2,2'-Bithiophene,5,5'-dimethyl- Structure

2,2'-Bithiophen...

5'-chloro-5-methyl-2,2'-bithiophene Structure

5'-chloro-5-met...

Benzoxazole Structure

2,5-Dibromothiophene Structure

2,5-Dibromothiophene

~49%

2,2'-thiophene-2,5-diylbis(benzoxazole) Structure

2,2'-thiophene-...

2-Bromo-6-methylpyridine Structure

2-Bromo-6-methy...

Benzoxazole Structure

~0%

6,6'-Dimethyl-2,2'-bipyridine Structure

6,6'-Dimethyl-2...

2-(6-methylpyridin-2-yl)-benzooxazole Structure

2-(6-methylpyri...

2-Bromo-6-methylpyridine Structure

2-Bromo-6-methy...

Benzo[d]thiazole Structure

Benzo[d]thiazole

~0%

2-(6-methylpyridin-2-yl)-1,3-benzothiazole Structure

2-(6-methylpyri...

6,6'-Dimethyl-2,2'-bipyridine Structure

6,6'-Dimethyl-2...

2-Chlorothiophene Structure

2-Chlorothiophene

2-Bromo-6-methylpyridine Structure

2-Bromo-6-methy...

~0%

6,6'-Dimethyl-2,2'-bipyridine Structure

6,6'-Dimethyl-2...

2-(5-chlorothiophen-2-yl)-6-methylpyridine Structure

2-(5-chlorothio...

2-Butylfuran Structure

2-Bromo-6-methylpyridine Structure

2-Bromo-6-methy...

~0%

6,6'-Dimethyl-2,2'-bipyridine Structure

6,6'-Dimethyl-2...

2-(5-butylfuran-2-yl)-6-methylpyridine Structure

2-(5-butylfuran...

2-Butylthiophene Structure

2-Butylthiophene

2-Bromo-6-methylpyridine Structure

2-Bromo-6-methy...

~0%

6,6'-Dimethyl-2,2'-bipyridine Structure

6,6'-Dimethyl-2...

2-(5-butylthiophen-2-yl)-6-methylpyridine Structure

2-(5-butylthiop...

2-Bromo-6-methylpyridine Structure

2-Bromo-6-methy...

1-Methylbenzimidazole Structure

1-Methylbenzimi...

~0%

6,6'-Dimethyl-2,2'-bipyridine Structure

6,6'-Dimethyl-2...

1-methyl-2-(6-methylpyridin-2-yl)benzimidazole Structure

1-methyl-2-(6-m...

2-Butylfuran Structure

5-Bromo-2-thiophenecarbaldehyde Structure

5-Bromo-2-thiop...

~0%

[2,2’]bithiophenyl-5,5'-dicarbaldehyde Structure

[2,2’]bithiophe...

5-(5-butylfuran-2-yl)thiophene-2-carbaldehyde Structure

5-(5-butylfuran...

methylthiol Structure

5-Bromo-2-thiophenecarbaldehyde Structure

5-Bromo-2-thiop...

~0%

[2,2’]bithiophenyl-5,5'-dicarbaldehyde Structure

[2,2’]bithiophe...

5-(5-methylthiophen-2-yl)thiophene-2-carbaldehyde Structure

5-(5-methylthio...

2-Chlorothiophene Structure

2-Chlorothiophene

5-Bromo-2-thiophenecarbaldehyde Structure

5-Bromo-2-thiop...

~0%

[2,2’]bithiophenyl-5,5'-dicarbaldehyde Structure

[2,2’]bithiophe...

5-(5-Chlorothiophen-2-yl)thiophene-2-carbaldehyde Structure

5-(5-Chlorothio...

2-Butylthiophene Structure

2-Butylthiophene

5-Bromo-2-thiophenecarbaldehyde Structure

5-Bromo-2-thiop...

~0%

[2,2’]bithiophenyl-5,5'-dicarbaldehyde Structure

[2,2’]bithiophe...

5'-butyl-2,2'-bithiophene-2-carbaldehyde Structure

5'-butyl-2,2'-b...

5-Bromo-2-thiophenecarbaldehyde Structure

5-Bromo-2-thiop...

methyl 2-methyl-3-furoate Structure

methyl 2-methyl...

~0%

[2,2’]bithiophenyl-5,5'-dicarbaldehyde Structure

[2,2’]bithiophe...

methyl 5-(5-formylthiophen-2-yl)-2-methylfuran-3-carboxylate Structure

methyl 5-(5-for...

Bromothiophene Structure

Benzoxazole Structure

~0%

2-(thiophen-2-yl)benzo[d]oxazole Structure

2-(thiophen-2-y...

2,2'-Bithiophene Structure

2,2'-Bithiophene

2-Butylthiophene Structure

2-Butylthiophene

2-Acetyl-5-bromothiophene Structure

2-Acetyl-5-brom...

~0%

Ethanone, 1,1'-[2,2'-bithiophene]-5,5'-diylbis- Structure

Ethanone, 1,1'-...

1-(5'-butyl-2,2'-bithiophene-5-yl)ethanone Structure

1-(5'-butyl-2,2...

methylthiol Structure

2-Acetyl-5-bromothiophene Structure

2-Acetyl-5-brom...

~0%

Ethanone, 1,1'-[2,2'-bithiophene]-5,5'-diylbis- Structure

Ethanone, 1,1'-...

1-(5'-methyl-2,2'-bithiophene-5-yl)ethanone Structure

1-(5'-methyl-2,...

2-Chlorothiophene Structure

2-Chlorothiophene

2-Acetyl-5-bromothiophene Structure

2-Acetyl-5-brom...

~0%

Ethanone, 1,1'-[2,2'-bithiophene]-5,5'-diylbis- Structure

Ethanone, 1,1'-...

1-(5'-chloro-2,2'-bithiophene-5-yl)ethanone Structure

1-(5'-chloro-2,...

2-Butylfuran Structure

2-Acetyl-5-bromothiophene Structure

2-Acetyl-5-brom...

~0%

Ethanone, 1,1'-[2,2'-bithiophene]-5,5'-diylbis- Structure

Ethanone, 1,1'-...

1-(5-(5-butylfuran-2-yl)thiophen-2-yl)ethanone Structure

1-(5-(5-butylfu...

2-Acetyl-5-bromothiophene Structure

2-Acetyl-5-brom...

2-propyl thiazole Structure

2-propyl thiazole

~0%

Ethanone, 1,1'-[2,2'-bithiophene]-5,5'-diylbis- Structure

Ethanone, 1,1'-...

1-[5-(2-propylthiazol-5-yl)thiophen-2-yl]ethanone Structure

1-[5-(2-propylt...

2-Acetyl-5-bromothiophene Structure

2-Acetyl-5-brom...

methyl 2-methyl-3-furoate Structure

methyl 2-methyl...

~0%

Ethanone, 1,1'-[2,2'-bithiophene]-5,5'-diylbis- Structure

Ethanone, 1,1'-...

methyl 5-(5-acetylthiophen-2-yl)-2-methylfuran-3-carboxylate Structure

methyl 5-(5-ace...

1-(Furan-2-yl)ethanone Structure

1-(Furan-2-yl)e...

2-Acetyl-5-bromothiophene Structure

2-Acetyl-5-brom...

~0%

Ethanone, 1,1'-[2,2'-bithiophene]-5,5'-diylbis- Structure

Ethanone, 1,1'-...

1-[5-(5-acetylfuran-2-yl)thiophen-2-yl]ethanone Structure

1-[5-(5-acetylf...

Palladium-catalyzed direct heteroarylation of chloropyridine...

[Derridj, Fazia; Roger, Julien; Geneste, Florence; Djebbar, Safia; Doucet, Henri Journal of Organometallic Chemistry, 2009 , vol. 694, # 3 p. 455 - 465]

2??(Methylpyridyl or quinolyl) benz??X??azoles

[Barni,E.; Savarino,P. Journal of Heterocyclic Chemistry, 1977 , vol. 14, p. 937 - 940]