Tetrahedron Letters

Rhodium-catalyzed phenylthiolation reaction of heteroaromatic compounds using α-(phenylthio) isobutyrophenone

M Arisawa, F Toriyama, M Yamaguchi

Index: Arisawa, Mieko; Toriyama, Fumihiko; Yamaguchi, Masahiko Tetrahedron Letters, 2011 , vol. 52, # 18 p. 2344 - 2347

Full Text: HTML

Citation Number: 23

Abstract

In the presence of catalytic amounts of RhH (PPh3) 4 and 1, 2-bis (diphenylphosphino) ethane (dppe), 1, 3-benzothiazoles, 1, 3-benzoxazoles, and benzothiophene reacted with α- (phenylthio) isobutyrophenone giving 2-phenylthio derivatives. Reactive monocyclic heteroaromatics, 1-methyl-1, 2, 3, 4-tetrazole and 2-cyanothiophene were also converted into the 5-phenylthio derivatives. The use of an appropriate phenylthio transfer reagent is ...

 Related Synthetic Route
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

N/A Structure

1300105-80-9

N/A

~0%

2-Methylmercaptobenzothiazole Structure

615-22-5

2-Methylmercapt...

1-propanone, 1-(4-methoxyphenyl)-2-methyl Structure

2040-20-2

1-propanone, 1-...

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

~91%

2-phenylsulfanyl-1,3-benzothiazole Structure

4276-60-2

2-phenylsulfany...

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
N/A Structure

20637-27-8

N/A

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

~93%

2-phenylsulfanyl-1,3-benzothiazole Structure

4276-60-2

2-phenylsulfany...

isobutyrophenone-d3 Structure

100649-48-7

isobutyrophenone-d3

Learn More
Thiophenol Structure

108-98-5

Thiophenol

~%

2-phenylsulfanyl-1,3-benzothiazole Structure

4276-60-2

2-phenylsulfany...

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

2-(methylthio)-1-phenyl-1-propanone Structure

14236-72-7

2-(methylthio)-...

~0%

2-Methylmercaptobenzothiazole Structure

615-22-5

2-Methylmercapt...

Phenyl ethyl ketone Structure

93-55-0

Phenyl ethyl ketone

Learn More
α-Bromoisobutyrophenone Structure

10409-54-8

α-Bromoisobutyr...

Thiophenol Structure

108-98-5

Thiophenol

~98%

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

N/A Structure

59919-17-4

N/A

~26%

2-(4-chlorophenyl)sulfanyl-1,3-benzothiazole Structure

39544-83-7

2-(4-chlorophen...

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

N/A Structure

1300105-81-0

N/A

~0%

2-Methylmercaptobenzothiazole Structure

615-22-5

2-Methylmercapt...

2,4'-dimethylpropiophenone Structure

50390-51-7

2,4'-dimethylpr...

Learn More
Benzoxazole Structure

273-53-0

Benzoxazole

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

~0%

N/A Structure

123773-64-8

N/A

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
6-Methyl-Benzothiazole Structure

2942-15-6

6-Methyl-Benzot...

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

~0%

6-methyl-2-(phenylthio)benzo[d]thiazole Structure

1189350-86-4

6-methyl-2-(phe...

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
6-Chloro-1,3-benzothiazole Structure

2942-10-1

6-Chloro-1,3-be...

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

~0%

6-chloro-2-(phenylthio)benzo[d]thiazole Structure

1189350-90-0

6-chloro-2-(phe...

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

6-TRIFLUOROMETHYLBENZOTHIAZOLE Structure

131106-70-2

6-TRIFLUOROMETH...

~0%

N/A Structure

1300105-94-5

N/A

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

5-Chlorobenzoxazole Structure

17200-29-2

5-Chlorobenzoxazole

~0%

5-chloro-2-phenylthio-1,3-benzoxazole Structure

1158999-45-1

5-chloro-2-phen...

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
5-METHYLBENZOXAZOLE Structure

10531-78-9

5-METHYLBENZOXAZOLE

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

~0%

5-methyl-2-phenylthio-1,3-benzoxazole Structure

1158999-40-6

5-methyl-2-phen...

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
Benzo[b]thiophene-3-carbonitrile Structure

24434-84-2

Benzo[b]thiophe...

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

~0%

N/A Structure

1300106-12-0

N/A

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
6-Methoxybenzo[d]oxazole Structure

114980-26-6

6-Methoxybenzo[...

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

~0%

N/A Structure

1300106-06-2

N/A

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
6-Methoxybenzo[d]thiazole Structure

2942-13-4

6-Methoxybenzo[...

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

~0%

6-Methoxy-2-(phenylthio)benzothiazole Structure

3507-20-8

6-Methoxy-2-(ph...

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

5-(Trifluoromethyl)benzoxazole Structure

1267217-46-8

5-(Trifluoromet...

~0%

N/A Structure

1300106-05-1

N/A

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

N/A Structure

59919-17-4

N/A

~0%

2-(4-chlorophenyl)sulfanyl-1,3-benzothiazole Structure

39544-83-7

2-(4-chlorophen...

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
Thiophen-2-carbonitril Structure

1003-31-2

Thiophen-2-carb...

2-methyl-1-phenyl-2-phenylsulfanylpropan-1-one Structure

59919-11-8

2-methyl-1-phen...

~0%

N/A Structure

1300106-13-1

N/A

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

N/A Structure

1300105-88-7

N/A

~0%

N/A Structure

1300105-89-8

N/A

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Learn More
N/A Structure

123773-64-8

N/A

Phenyl ethyl ketone Structure

93-55-0

Phenyl ethyl ketone

~16%

Benzoxazole Structure

273-53-0

Benzoxazole

1-phenyl-2-(phenylthio)-1-propanone Structure

28403-86-3

1-phenyl-2-(phe...

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

N/A Structure

1300105-81-0

N/A

~23%

2-Methylmercaptobenzothiazole Structure

615-22-5

2-Methylmercapt...

2,4'-dimethylpropiophenone Structure

50390-51-7

2,4'-dimethylpr...

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

N/A Structure

1300105-82-1

N/A

~15%

2-Methylmercaptobenzothiazole Structure

615-22-5

2-Methylmercapt...

1-(4-Chlorophenyl)-2-methyl-1-propanone Structure

18713-58-1

1-(4-Chlorophen...

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

N/A Structure

1300105-80-9

N/A

~21%

2-Methylmercaptobenzothiazole Structure

615-22-5

2-Methylmercapt...

1-propanone, 1-(4-methoxyphenyl)-2-methyl Structure

2040-20-2

1-propanone, 1-...

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

2-(methylthio)-1-phenyl-1-propanone Structure

14236-72-7

2-(methylthio)-...

~13%

2-Methylmercaptobenzothiazole Structure

615-22-5

2-Methylmercapt...

Phenyl ethyl ketone Structure

93-55-0

Phenyl ethyl ketone

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

N/A Structure

1300105-83-2

N/A

~9%

2-Methylmercaptobenzothiazole Structure

615-22-5

2-Methylmercapt...

4-isobutyrylbenzonitrile Structure

79341-95-0

4-isobutyrylben...

Learn More
2-Phenylacetophenone Structure

451-40-1

2-Phenylacetophenone

α-(methylthio)-p-cyanoacetophenone Structure

1114817-69-4

α-(methylthio)-...

~70%

P-CYANOACETOPHENONE Structure

1443-80-7

P-CYANOACETOPHENONE

2-methylsulfanyl-1,2-diphenyl-ethanone Structure

32368-19-7

2-methylsulfany...

Learn More
Benzo[d]thiazole Structure

95-16-9

Benzo[d]thiazole

N/A Structure

1300105-82-1

N/A

~0%

2-Methylmercaptobenzothiazole Structure

615-22-5

2-Methylmercapt...

1-(4-Chlorophenyl)-2-methyl-1-propanone Structure

18713-58-1

1-(4-Chlorophen...

Learn More

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