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

Tetrahedron Letters

Unsymmetrical ketone synthesis via palladium catalyzed carbonylation of organic halides

Y Tamaru, H Ochiai, Y Yamada, Z Yoshida

Index: Tamaru, Yoshinao; Ochiai, Hirofumi; Yamada, Yoshimi; Yoshida, Zen-ichi Tetrahedron Letters, 1983 , vol. 24, # 36 p. 3869 - 3872

Full Text: HTML

Citation Number: 54

Abstract

Abstract Aryl alkyl (or benzyl) ketones are selectively prepared by the reaction of aryl iodides and alkyl iodides (or benzyl chlorides) in the presence of a stoichiometric amount of zinc- copper couple and a catalytic amount of palladium (0) complex under an atmospheric pressure of carbon monoxide.

Iodobenzene Structure

1-Iodo-2-methylpropane Structure

1-Iodo-2-methyl...

carbon monoxide Structure

carbon monoxide

~83%

Isovalerophenone Structure

Isovalerophenone

4-Iodoanisole Structure

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~81%

Bis(p-chlorophenyl)ethane Structure

Bis(p-chlorophe...

(4-chlorophenyl)-4-methoxyphenylmethane Structure

(4-chlorophenyl...

Detail

carbon monoxide Structure

carbon monoxide

4-Iodoanisole Structure

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~81%

Bis(p-chlorophenyl)ethane Structure

Bis(p-chlorophe...

Detail

Methyl 2-iodobenzoate Structure

Methyl 2-iodobe...

~23%

Methyl benzoate Structure

Methyl benzoate

[1,1'-Biphenyl]-2,2'-dicarboxylicacid, 2,2'-dimethyl ester Structure

[1,1'-Biphenyl]...

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~26%

Methyl benzoate Structure

Methyl benzoate

Bis(p-chlorophenyl)ethane Structure

Bis(p-chlorophe...

[1,1'-Biphenyl]-2,2'-dicarboxylicacid, 2,2'-dimethyl ester Structure

[1,1'-Biphenyl]...

Detail

Methyl 2-iodobenzoate Structure

Methyl 2-iodobe...

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~26%

Methyl benzoate Structure

Methyl benzoate

2-(p-Chlorbenzyl)benzoesaeuremethylester Structure

2-(p-Chlorbenzy...

Detail

carbon monoxide Structure

carbon monoxide

Methyl 2-iodobenzoate Structure

Methyl 2-iodobe...

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~26%

Methyl benzoate Structure

Methyl benzoate

Detail

Iodobenzene Structure

carbon monoxide Structure

carbon monoxide

1-Iodopropane Structure

~90%

1-Phenylbutan-1-one Structure

1-Phenylbutan-1-one

carbon monoxide Structure

carbon monoxide

4-Iodoanisole Structure

1-Iodopropane Structure

~88%

4'-Methoxybutyrophenone Structure

4'-Methoxybutyr...

1-Bromo-4-iodobenzene Structure

1-Bromo-4-iodob...

~39%

p-Bromobutyrophenone Structure

p-Bromobutyrophenone

4,4'-Dibromobiphenyl Structure

4,4'-Dibromobiphenyl

4,4'-Dibromobenzophenone Structure

4,4'-Dibromoben...

carbon monoxide Structure

carbon monoxide

1-Bromo-4-iodobenzene Structure

1-Bromo-4-iodob...

1-Iodopropane Structure

~38%

p-Bromobutyrophenone Structure

p-Bromobutyrophenone

Detail

carbon monoxide Structure

carbon monoxide

1-Bromo-4-iodobenzene Structure

1-Bromo-4-iodob...

~38%

p-Bromobutyrophenone Structure

p-Bromobutyrophenone

4,4'-Dibromobiphenyl Structure

4,4'-Dibromobiphenyl

Detail

4-Iodotoluene Structure

carbon monoxide Structure

carbon monoxide

~57%

2,2'-Dimethylbenzophenone Structure

2,2'-Dimethylbe...

1-(2-methylphenyl)butan-1-one Structure

1-(2-methylphen...

4-Iodotoluene Structure

carbon monoxide Structure

carbon monoxide

1-Iodopropane Structure

~56%

2,2'-Dimethylbenzophenone Structure

2,2'-Dimethylbe...

Detail

carbon monoxide Structure

carbon monoxide

4-Iodotoluene Structure

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~1%

2-(4-chlorophenyl)-1-(p-tolyl)ethanone Structure

2-(4-chlorophen...

Detail

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~17%

Methyl benzoate Structure

Methyl benzoate

Bis(p-chlorophenyl)ethane Structure

Bis(p-chlorophe...

[1,1'-Biphenyl]-2,2'-dicarboxylicacid, 2,2'-dimethyl ester Structure

[1,1'-Biphenyl]...

Detail

carbon monoxide Structure

carbon monoxide

Methyl 2-iodobenzoate Structure

Methyl 2-iodobe...

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~18%

Methyl benzoate Structure

Methyl benzoate

Detail

carbon monoxide Structure

carbon monoxide

4-Iodotoluene Structure

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~65%

2-(4-chlorophenyl)-1-(p-tolyl)ethanone Structure

2-(4-chlorophen...

Detail

2-Iodopropane Structure

Iodobenzene Structure

carbon monoxide Structure

carbon monoxide

~85%

Cumene Structure

Detail

2-Iodopropane Structure

Iodobenzene Structure

carbon monoxide Structure

carbon monoxide

~0%

Cumene Structure

Detail

4-Iodoanisole Structure

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~9%

Bis(p-chlorophenyl)ethane Structure

Bis(p-chlorophe...

(4-chlorophenyl)-4-methoxyphenylmethane Structure

(4-chlorophenyl...

Detail

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~26%

Methyl benzoate Structure

Methyl benzoate

Bis(p-chlorophenyl)ethane Structure

Bis(p-chlorophe...

[1,1'-Biphenyl]-2,2'-dicarboxylicacid, 2,2'-dimethyl ester Structure

[1,1'-Biphenyl]...

Detail

Methyl 2-iodobenzoate Structure

Methyl 2-iodobe...

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~27%

Methyl benzoate Structure

Methyl benzoate

2-(p-Chlorbenzyl)benzoesaeuremethylester Structure

2-(p-Chlorbenzy...

Detail

carbon monoxide Structure

carbon monoxide

Methyl 2-iodobenzoate Structure

Methyl 2-iodobe...

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~27%

Methyl benzoate Structure

Methyl benzoate

Detail

carbon monoxide Structure

carbon monoxide

4-Iodoanisole Structure

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~8%

Bis(p-chlorophenyl)ethane Structure

Bis(p-chlorophe...

Detail

Iodobenzene Structure

carbon monoxide Structure

carbon monoxide

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~14%

Benzene,1-chloro-4-(phenylmethyl)- Structure

Benzene,1-chlor...

Detail

carbon monoxide Structure

carbon monoxide

4-Iodotoluene Structure

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~9%

2-(4-chlorophenyl)-1-(p-tolyl)ethanone Structure

2-(4-chlorophen...

Detail

carbon monoxide Structure

carbon monoxide

4-Iodotoluene Structure

1-Iodopropane Structure

~89%

p-Methylbutyrophenone Structure

p-Methylbutyrop...

Palladium??Catalyzed Synthesis of Aryl Ketones from Boronic ...

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Catalytic cross-coupling of alkylzinc halides with α-chlorok...

[Malosh, Chrysa F.; Ready, Joseph M. Journal of the American Chemical Society, 2004 , vol. 126, # 33 p. 10240 - 10241]

Selenium-assisted reduction of α-and β-diketones with carbon...

[Tetrahedron Letters, , vol. 33, # 42 p. 6347 - 6350]

Ionic hydrogenation of α, β-unsaturated ketones with cyclohe...

[Koltunov; Repinskaya; Borodkin Russian Journal of Organic Chemistry, 2001 , vol. 37, # 11 p. 1534 - 1541]

Synthetic Utility of Stannyl Enolates as Radical Alkylating ...

[Miura, Katsukiyo; Fujisawa, Naoki; Saito, Hiroshi; Wang, Di; Hosomi, Akira Organic Letters, 2001 , vol. 3, # 16 p. 2591 - 2594]