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

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 ...

Benzo[d]thiazole Structure

Benzo[d]thiazole

N/A Structure

~0%

2-Methylmercaptobenzothiazole Structure

2-Methylmercapt...

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

1-propanone, 1-...

Benzo[d]thiazole Structure

Benzo[d]thiazole

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

2-methyl-1-phen...

~91%

2-phenylsulfanyl-1,3-benzothiazole Structure

2-phenylsulfany...

Isobutyrophenone Structure

Isobutyrophenone

N/A Structure

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

2-methyl-1-phen...

~93%

2-phenylsulfanyl-1,3-benzothiazole Structure

2-phenylsulfany...

isobutyrophenone-d3 Structure

isobutyrophenone-d3

Thiophenol Structure

~%

2-phenylsulfanyl-1,3-benzothiazole Structure

2-phenylsulfany...

Benzo[d]thiazole Structure

Benzo[d]thiazole

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

2-(methylthio)-...

~0%

2-Methylmercaptobenzothiazole Structure

2-Methylmercapt...

Phenyl ethyl ketone Structure

Phenyl ethyl ketone

α-Bromoisobutyrophenone Structure

α-Bromoisobutyr...

Thiophenol Structure

~98%

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

2-methyl-1-phen...

Benzo[d]thiazole Structure

Benzo[d]thiazole

N/A Structure

~26%

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

2-(4-chlorophen...

Isobutyrophenone Structure

Isobutyrophenone

Benzo[d]thiazole Structure

Benzo[d]thiazole

N/A Structure

~0%

2-Methylmercaptobenzothiazole Structure

2-Methylmercapt...

2,4'-dimethylpropiophenone Structure

2,4'-dimethylpr...

Benzoxazole Structure

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

2-methyl-1-phen...

~0%

N/A Structure

Isobutyrophenone Structure

Isobutyrophenone

6-Methyl-Benzothiazole Structure

6-Methyl-Benzot...

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

2-methyl-1-phen...

~0%

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

6-methyl-2-(phe...

Isobutyrophenone Structure

Isobutyrophenone

6-Chloro-1,3-benzothiazole Structure

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

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

2-methyl-1-phen...

~0%

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

6-chloro-2-(phe...

Isobutyrophenone Structure

Isobutyrophenone

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

2-methyl-1-phen...

6-TRIFLUOROMETHYLBENZOTHIAZOLE Structure

6-TRIFLUOROMETH...

~0%

N/A Structure

Isobutyrophenone Structure

Isobutyrophenone

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

2-methyl-1-phen...

5-Chlorobenzoxazole Structure

5-Chlorobenzoxazole

~0%

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

5-chloro-2-phen...

Isobutyrophenone Structure

Isobutyrophenone

5-METHYLBENZOXAZOLE Structure

5-METHYLBENZOXAZOLE

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

2-methyl-1-phen...

~0%

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

5-methyl-2-phen...

Isobutyrophenone Structure

Isobutyrophenone

Benzo[b]thiophene-3-carbonitrile Structure

Benzo[b]thiophe...

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

2-methyl-1-phen...

~0%

N/A Structure

Isobutyrophenone Structure

Isobutyrophenone

6-Methoxybenzo[d]oxazole Structure

6-Methoxybenzo[...

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

2-methyl-1-phen...

~0%

N/A Structure

Isobutyrophenone Structure

Isobutyrophenone

6-Methoxybenzo[d]thiazole Structure

6-Methoxybenzo[...

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

2-methyl-1-phen...

~0%

6-Methoxy-2-(phenylthio)benzothiazole Structure

6-Methoxy-2-(ph...

Isobutyrophenone Structure

Isobutyrophenone

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

2-methyl-1-phen...

5-(Trifluoromethyl)benzoxazole Structure

5-(Trifluoromet...

~0%

N/A Structure

Isobutyrophenone Structure

Isobutyrophenone

Benzo[d]thiazole Structure

Benzo[d]thiazole

N/A Structure

~0%

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

2-(4-chlorophen...

Isobutyrophenone Structure

Isobutyrophenone

Thiophen-2-carbonitril Structure

Thiophen-2-carb...

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

2-methyl-1-phen...

~0%

N/A Structure

Isobutyrophenone Structure

Isobutyrophenone

Benzo[d]thiazole Structure

Benzo[d]thiazole

N/A Structure

~0%

N/A Structure

Isobutyrophenone Structure

Isobutyrophenone

N/A Structure

Phenyl ethyl ketone Structure

Phenyl ethyl ketone

~16%

Benzoxazole Structure

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

1-phenyl-2-(phe...

Benzo[d]thiazole Structure

Benzo[d]thiazole

N/A Structure

~23%

2-Methylmercaptobenzothiazole Structure

2-Methylmercapt...

2,4'-dimethylpropiophenone Structure

2,4'-dimethylpr...

Benzo[d]thiazole Structure

Benzo[d]thiazole

N/A Structure

~15%

2-Methylmercaptobenzothiazole Structure

2-Methylmercapt...

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

1-(4-Chlorophen...

Benzo[d]thiazole Structure

Benzo[d]thiazole

N/A Structure

~21%

2-Methylmercaptobenzothiazole Structure

2-Methylmercapt...

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

1-propanone, 1-...

Benzo[d]thiazole Structure

Benzo[d]thiazole

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

2-(methylthio)-...

~13%

2-Methylmercaptobenzothiazole Structure

2-Methylmercapt...

Phenyl ethyl ketone Structure

Phenyl ethyl ketone

Benzo[d]thiazole Structure

Benzo[d]thiazole

N/A Structure

~9%

2-Methylmercaptobenzothiazole Structure

2-Methylmercapt...

4-isobutyrylbenzonitrile Structure

4-isobutyrylben...

2-Phenylacetophenone Structure

2-Phenylacetophenone

α-(methylthio)-p-cyanoacetophenone Structure

α-(methylthio)-...

~70%

P-CYANOACETOPHENONE Structure

P-CYANOACETOPHENONE

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

2-methylsulfany...

Benzo[d]thiazole Structure

Benzo[d]thiazole

N/A Structure

~0%

2-Methylmercaptobenzothiazole Structure

2-Methylmercapt...

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

1-(4-Chlorophen...

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