Cycloisomerization of 2??Alkynylanilines to Indoles Catalyzed by Carbon??Supported Gold Nanoparticles and Subsequent Homocoupling to 3, 3′??Biindoles

…, N Huittinen, JA Lopez??Sanchez…

Index: Perea-Buceta, Jesus E.; Wirtanen, Tom; Laukkanen, Otto-Ville; Maekelae, Mikko K.; Nieger, Martin; Melchionna, Michele; Huittinen, Nina; Lopez-Sanchez, Jose A.; Helaja, Juho Angewandte Chemie - International Edition, 2013 , vol. 52, # 45 p. 11835 - 11839 Angew. Chem., 2013 , vol. 125, # 45 p. 12051 - 12055,5

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Citation Number: 27

Abstract

Construction of biologically and pharmaceutically important indole moieties plays a prominent role in classic organic synthesis and modern catalysis. This role is not only due to the significance of the potential applications but also as a standard to calibrate the efficiency of a given method.[1, 2] Despite the fact that the cycloisomerization of 2-alkynylanilines provides one of the most direct and atom-economical manners to assemble indoles,[3, 4] ...

 Related Synthetic Route
2-(phenylethynyl)aniline Structure

13141-38-3

2-(phenylethyny...

~0%

2-Phenylindole Structure

948-65-2

2-Phenylindole

3,3'-Bi-1H-indole,2,2'-diphenyl Structure

2415-33-0

3,3'-Bi-1H-indo...

Learn More
2-Iodoaniline Structure

615-43-0

2-Iodoaniline

~%

2-Phenylindole Structure

948-65-2

2-Phenylindole

3,3'-Bi-1H-indole,2,2'-diphenyl Structure

2415-33-0

3,3'-Bi-1H-indo...

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Phenylacetylene Structure

536-74-3

Phenylacetylene

~%

2-Phenylindole Structure

948-65-2

2-Phenylindole

3,3'-Bi-1H-indole,2,2'-diphenyl Structure

2415-33-0

3,3'-Bi-1H-indo...

Learn More
1-ETHYNYL-2,3,4,5,6-PENTAFLUORO-BENZENE Structure

5122-07-6

1-ETHYNYL-2,3,4...

2-Iodoaniline Structure

615-43-0

2-Iodoaniline

~%

2-(2,3,4,5,6-pentafluorophenyl)-1H-indole Structure

116993-61-4

2-(2,3,4,5,6-pe...

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1-Iodo-4-nitrobenzene Structure

636-98-6

1-Iodo-4-nitrob...

2-Ethynylaniline Structure

52670-38-9

2-Ethynylaniline

~10%

2-[2-(4-nitrophenyl)ethynyl]aniline Structure

157869-12-0

2-[2-(4-nitroph...

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4-Chloro-2-(phenylethynyl)aniline Structure

928782-97-2

4-Chloro-2-(phe...

~98%

5-Chloro-2-phenyl-1H-indole Structure

23746-76-1

5-Chloro-2-phen...

Learn More
N/A Structure

960608-47-3

N/A

~96%

6-Chloro-2-phenyl-1H-indole Structure

57039-63-1

6-Chloro-2-phen...

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2-Iodoaniline Structure

615-43-0

2-Iodoaniline

Hex-1-yne Structure

693-02-7

Hex-1-yne

~%

1H-Indole, 2-propyl Structure

13228-41-6

1H-Indole, 2-propyl

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2-[(4-Methylphenyl)ethynyl]aniline Structure

124643-45-4

2-[(4-Methylphe...

~93%

1H-Indole,2-(4-methylphenyl) Structure

55577-25-8

1H-Indole,2-(4-...

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2-[(4-Methylphenyl)ethynyl]aniline Structure

124643-45-4

2-[(4-Methylphe...

~0%

1H-Indole,2-(4-methylphenyl) Structure

55577-25-8

1H-Indole,2-(4-...

2,2'-di(p-tolyl)-1H,1'H-3,3'-biindole Structure

1262302-49-7

2,2'-di(p-tolyl...

Learn More
2-Iodoaniline Structure

615-43-0

2-Iodoaniline

~%

1H-Indole,2-(4-methylphenyl) Structure

55577-25-8

1H-Indole,2-(4-...

2,2'-di(p-tolyl)-1H,1'H-3,3'-biindole Structure

1262302-49-7

2,2'-di(p-tolyl...

Learn More
4-Ethynyltoluene Structure

766-97-2

4-Ethynyltoluene

~%

1H-Indole,2-(4-methylphenyl) Structure

55577-25-8

1H-Indole,2-(4-...

2,2'-di(p-tolyl)-1H,1'H-3,3'-biindole Structure

1262302-49-7

2,2'-di(p-tolyl...

Learn More
2-((4-fluorophenyl)ethynyl)benzeneaMine Structure

1173153-20-2

2-((4-fluorophe...

~90%

2-(4-Fluorophenyl) indole Structure

782-17-2

2-(4-Fluorophen...

Learn More
2-((4-fluorophenyl)ethynyl)benzeneaMine Structure

1173153-20-2

2-((4-fluorophe...

~0%

2,2'-bis(4-fluorophenyl)-1H,1'H-3,3'-biindole Structure

1262302-60-2

2,2'-bis(4-fluo...

2-(4-Fluorophenyl) indole Structure

782-17-2

2-(4-Fluorophen...

Learn More
2-Iodoaniline Structure

615-43-0

2-Iodoaniline

~%

3-(2-chlorophenyl)-5-(4-phenylcyclohexyl)-1,2,4-oxadiazole Structure

5784-95-2

3-(2-chlorophen...

N/A Structure

1262302-54-4

N/A

Learn More
Phenylacetylene Structure

536-74-3

Phenylacetylene

~%

3-(2-chlorophenyl)-5-(4-phenylcyclohexyl)-1,2,4-oxadiazole Structure

5784-95-2

3-(2-chlorophen...

N/A Structure

1262302-54-4

N/A

Learn More
ethynylpyridine Structure

1945-84-2

ethynylpyridine

2-Iodoaniline Structure

615-43-0

2-Iodoaniline

~74%

2-(2-pyridin-2-ylethynyl)aniline Structure

13141-43-0

2-(2-pyridin-2-...

Learn More
2-(phenylethynyl)aniline Structure

13141-38-3

2-(phenylethyny...

~86%

2-Phenylindole Structure

948-65-2

2-Phenylindole

3,3'-Bi-1H-indole,2,2'-diphenyl Structure

2415-33-0

3,3'-Bi-1H-indo...

Learn More
2-(phenylethynyl)aniline Structure

13141-38-3

2-(phenylethyny...

~0%

3-(2-chlorophenyl)-5-(4-phenylcyclohexyl)-1,2,4-oxadiazole Structure

5784-95-2

3-(2-chlorophen...

N/A Structure

1262302-54-4

N/A

Learn More
2-[(4-Methoxyphenyl)ethynyl]aniline Structure

157869-15-3

2-[(4-Methoxyph...

~80%

3-(2-chlorophenyl)-5-(4-phenylcyclohexyl)-1,2,4-oxadiazole Structure

5784-95-2

3-(2-chlorophen...

N/A Structure

1262302-54-4

N/A

Learn More
4-Ethynylanisole Structure

768-60-5

4-Ethynylanisole

~%

3-(2-chlorophenyl)-5-(4-phenylcyclohexyl)-1,2,4-oxadiazole Structure

5784-95-2

3-(2-chlorophen...

N/A Structure

1262302-54-4

N/A

Learn More
Methyl 4-[2-(2-aminophenyl)ethynyl]benzoate Structure

159970-12-4

Methyl 4-[2-(2-...

~81%

Methyl 4-(1H-indol-2-yl)benzoate Structure

485321-10-6

Methyl 4-(1H-in...

Learn More
2-Iodoaniline Structure

615-43-0

2-Iodoaniline

methyl 4-ethynylbenzoate Structure

3034-86-4

methyl 4-ethyny...

~%

Methyl 4-(1H-indol-2-yl)benzoate Structure

485321-10-6

Methyl 4-(1H-in...

Learn More

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