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

Trans-chelating ligands in palladium-catalyzed carbonylative coupling and methoxycarbonylation of aryl halides

L Kaganovsky, D Gelman, K Rueck-Braun

Index: Kaganovsky, Luba; Gelman, Dmitri; Rueck-Braun, Karola Journal of Organometallic Chemistry, 2010 , vol. 695, # 2 p. 260 - 266

Full Text: HTML

Citation Number: 27

Abstract

The manuscript describes the use of a trans-chelated palladium complex derived from 1, 8- bis-(4-(diphenylphosphino) phenyl) anthracene (1) and p-TolPdI (TMEDA) as a precatalyst in carbonylative Suzuki coupling and methoxycarbonylation of aryl iodides and bromides. The catalyst is active in 0.01–1mol% loading and demonstrates highly selective transformations. The selectivity is attributed to the unique structural features of the trans- ...

1-Bromo-2-iodobenzene Structure

1-Bromo-2-iodob...

carbon monoxide Structure

carbon monoxide

Phenylboronic acid Structure

Phenylboronic acid

~0%

2-Bromobenzophenone Structure

2-Bromobenzophenone

Detail

1-Bromo-2-iodobenzene Structure

1-Bromo-2-iodob...

carbon monoxide Structure

carbon monoxide

4-Boronoanisole Structure

4-Boronoanisole

~0%

2-BROMO-3'-METHOXYBENZOPHENONE Structure

2-BROMO-3'-METH...

Detail

1-Bromo-2-iodobenzene Structure

1-Bromo-2-iodob...

carbon monoxide Structure

carbon monoxide

4-Boronoanisole Structure

4-Boronoanisole

~42%

2-BROMO-3'-METHOXYBENZOPHENONE Structure

2-BROMO-3'-METH...

Detail

4-Iodotoluene Structure

carbon monoxide Structure

carbon monoxide

Phenylboronic acid Structure

Phenylboronic acid

~97%

o-methylbenzophenone Structure

o-methylbenzophenone

1-Iodo-4-nitrobenzene Structure

1-Iodo-4-nitrob...

carbon monoxide Structure

carbon monoxide

(4-Chlorophenyl)boronic acid Structure

(4-Chlorophenyl...

~92%

4-chloro-4'-nitrobenzophenone Structure

4-chloro-4'-nit...

Methanol Structure

4-Bromoanisole Structure

carbon monoxide Structure

carbon monoxide

~96%

Methyl anisate Structure

1-Iodo-4-nitrobenzene Structure

1-Iodo-4-nitrob...

carbon monoxide Structure

carbon monoxide

m-Tolylboronic acid Structure

m-Tolylboronic acid

~92%

3-METHYL-4'-NITROBENZOPHENONE Structure

3-METHYL-4'-NIT...

Methanol Structure

carbon monoxide Structure

carbon monoxide

4-Bromobenzyl alcohol Structure

4-Bromobenzyl a...

~72%

Methyl (4-hydroxymethyl)benzoate Structure

Methyl (4-hydro...

carbon monoxide Structure

carbon monoxide

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

Phenylboronic acid Structure

Phenylboronic acid

~90%

1-(4-benzoylphenyl)ethanone Structure

1-(4-benzoylphe...

Methanol Structure

3-Iodoanisole Structure

carbon monoxide Structure

carbon monoxide

~99%

Methyl 3-methoxybenzoate Structure

Methyl 3-methox...

Iodobenzene Structure

carbon monoxide Structure

carbon monoxide

m-Tolylboronic acid Structure

m-Tolylboronic acid

~95%

3-Methylbenzophenone Structure

3-Methylbenzophenone

Methanol Structure

carbon monoxide Structure

carbon monoxide

1-Bromo-4-iodobenzene Structure

1-Bromo-4-iodob...

~93%

Methyl 4-bromobenzoate Structure

Methyl 4-bromob...

Iodobenzene Structure

carbon monoxide Structure

carbon monoxide

4-Boronoanisole Structure

4-Boronoanisole

~90%

3-Ethoxybenzophenone Structure

3-Ethoxybenzophenone

carbon monoxide Structure

carbon monoxide

4-Iodotoluene Structure

4-Boronoanisole Structure

4-Boronoanisole

~97%

(3-methoxyphenyl)-(4-methylphenyl)methanone Structure

(3-methoxypheny...

carbon monoxide Structure

carbon monoxide

4-Bromotoluene Structure

4-Boronoanisole Structure

4-Boronoanisole

~81%

(3-methoxyphenyl)-(4-methylphenyl)methanone Structure

(3-methoxypheny...

Methanol Structure

carbon monoxide Structure

carbon monoxide

3-Iodobenzonitrile Structure

3-Iodobenzonitrile

~86%

Methyl 3-cyanobenzoate Structure

Methyl 3-cyanob...

Methanol Structure

carbon monoxide Structure

carbon monoxide

1-Chloro-2-iodobenzene Structure

1-Chloro-2-iodo...

~97%

Methyl 2-chlorobenzoate Structure

Methyl 2-chloro...

Methanol Structure

diiodobenzene Structure

carbon monoxide Structure

carbon monoxide

~95%

Dimethyl phthalate Structure

Dimethyl phthalate

carbon monoxide Structure

carbon monoxide

1-Bromo-4-nitrobenzene Structure

1-Bromo-4-nitro...

Phenylboronic acid Structure

Phenylboronic acid

~77%

4-Nitrobenzophenone Structure

4-Nitrobenzophenone

carbon monoxide Structure

carbon monoxide

4-Iodotoluene Structure

(4-Chlorophenyl)boronic acid Structure

(4-Chlorophenyl...

~91%

4-Chloro-4'-methylbenzophenone Structure

4-Chloro-4'-met...

3-Bromopyridine Structure

3-Bromopyridine

Methanol Structure

carbon monoxide Structure

carbon monoxide

~93%

Methyl nicotinate Structure

Methyl nicotinate

Methanol Structure

1-Bromo-4-tert-butylbenzene Structure

1-Bromo-4-tert-...

carbon monoxide Structure

carbon monoxide

~88%

Methyl p-tert-butylbenzoate Structure

Methyl p-tert-b...

A facile method for the oxidation of aldehydes to carboxylic...

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Selectivities in reactions of organolithium reagents with ar...

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Cupric bromide as benzylic bromination reagent in polar medi...

[Synthetic Communications, , vol. 11, # 8 p. 669 - 672]

Effect of aldehyde and methoxy substituents on nucleophilic ...

[Journal of Fluorine Chemistry, , vol. 128, # 12 p. 1461 - 1468]

Substituent effects on the base-catalysed hydrolysis of phen...

[Collection of Czechoslovak Chemical Communications, , vol. 66, # 5 p. 770 - 784]