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

Reductive Carbonylation of Aryl Halides Employing a Two-Chamber Reactor: A Protocol for the Synthesis of Aryl Aldehydes Including 13C-and D-Isotope Labeling

…, RH Taaning, AT Lindhardt, T Skrydstrup

Index: Korsager, Signe; Taaning, Rolf H.; Lindhardt, Anders T.; Skrydstrup, Troels Journal of Organic Chemistry, 2013 , vol. 78, # 12 p. 6112 - 6120

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Citation Number: 31

Abstract

A protocol has been developed for conducting the palladium-catalyzed reductive carbonylation of aryl iodides and bromides using 9-methylfluorene-9-carbonyl chloride (COgen) as a source of externally delivered carbon monoxide in a sealed two-chamber system (COware), and potassium formate as the in situ hydride source. The method is tolerant to a wide number of functional groups positioned on the aromatic ring, and it can ...

Phenol,4-iodo-, 1-(4-methylbenzenesulfonate) Structure

Phenol,4-iodo-,...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~82%

4-[[(4-methylphenyl)sulfonyl]oxy]benzaldehyde Structure

4-[[(4-methylph...

1-bromo-4-(4-methylphenyl)sulfonyloxy-benzene Structure

1-bromo-4-(4-me...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~62%

4-[[(4-methylphenyl)sulfonyl]oxy]benzaldehyde Structure

4-[[(4-methylph...

Ethyl 4-iodobenzoate Structure

Ethyl 4-iodobenzoate

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~79%

Benzoic acid,4-formyl-, ethyl ester Structure

Benzoic acid,4-...

Ethyl 4-bromobenzoate Structure

Ethyl 4-bromobe...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~81%

Benzoic acid,4-formyl-, ethyl ester Structure

Benzoic acid,4-...

4-Bromoisoquinoline Structure

4-Bromoisoquinoline

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~44%

3-Isoquinolinecarboxaldehyde Structure

3-Isoquinolinec...

4-Iodo-1,2-dimethoxybenzene Structure

4-Iodo-1,2-dime...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~96%

veratraldehyde Structure

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

2-(4-Iodophenyl)-2-methyl-1,3-dioxolane Structure

2-(4-Iodophenyl...

~88%

4-(2-methyl-1,3-dioxolan-2-yl)benzaldehyde Structure

4-(2-methyl-1,3...

1-Fluoro-3-iodo-5-methylbenzene Structure

1-Fluoro-3-iodo...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~95%

3-Fluoro-5-methylbenzaldehyde Structure

3-Fluoro-5-meth...

(4-Bromophenyl)(4-morpholinyl)methanone Structure

(4-Bromophenyl)...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~73%

4-(Morpholine-4-Carbonyl)-Benzaldehyde Structure

4-(Morpholine-4...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

tert-butyl (4-iodophenyl)carbamate Structure

tert-butyl (4-i...

~76%

4-(Boc-amino)benzaldehyde Structure

4-(Boc-amino)be...

1-Bromo-4-butylbenzene Structure

1-Bromo-4-butyl...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~97%

4-Butylbenzaldehyde Structure

4-Butylbenzaldehyde

2,6-dichloro-4-iodoaniline Structure

2,6-dichloro-4-...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~80%

4-Amino-3,5-dichlorobenzaldehyde Structure

4-Amino-3,5-dic...

4-Iodobenzonitrile Structure

4-Iodobenzonitrile

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~87%

4-Cyanobenzaldehyde Structure

4-Cyanobenzaldehyde

(2H2)Formic acid Structure

(2H2)Formic acid

~98%

potassium,deuterioformate Structure

potassium,deute...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine Structure

6-Bromo-2,3-dih...

~78%

1,4-Benzodioxane-6-aldehyde Structure

1,4-Benzodioxan...

2,4-Dimethoxyiodobenzene Structure

2,4-Dimethoxyio...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~81%

2,4-dimethoxybenzaldehyde Structure

2,4-dimethoxybe...

Benzene, 5-iodo-1,2,3-trimethoxy- Structure

Benzene, 5-iodo...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~91%

3,4,5-Trimethoxybenzaldehyde Structure

3,4,5-Trimethox...

benzyl 3-iodo-1H-indole-1-carboxylate Structure

benzyl 3-iodo-1...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~67%

Indole-3-carboxaldehyde Structure

Indole-3-carbox...

4-Bromo-2-chloro-1-methoxybenzene Structure

4-Bromo-2-chlor...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~85%

3-CHLORO-4-METHOXYBENZALDEHYDE Structure

3-CHLORO-4-METH...

1-Iodo-4-(2-methyl-2-propanyl)benzene Structure

1-Iodo-4-(2-met...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~86%

p-t-Butylbenzaldehyde Structure

p-t-Butylbenzal...

4-Iodo-N-methylaniline Structure

4-Iodo-N-methyl...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~67%

4-(methylamino)benzaldehyde Structure

4-(methylamino)...

p-Hexyloxybromobenzene Structure

p-Hexyloxybromo...

9-Methylfluorene-9-carbonyl chloride Structure

9-Methylfluoren...

~69%

4-Hexoxybenzaldehyde Structure

4-Hexoxybenzaldehyde

Stereoselective synthesis of (+)-radicamine B

[Shankaraiah; Sateesh Chandra Kumar; Poornima; Babu, K. Suresh Tetrahedron Letters, 2011 , vol. 52, # 38 p. 4885 - 4887]