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

Organic letters

Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation

JC Wan, JM Huang, YH Jhan, JC Hsieh

Index: Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh Organic Letters, 2013 , vol. 15, # 11 p. 2742 - 2745

Full Text: HTML

Citation Number: 39

Abstract

Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C–H and dual C–H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.

4-Iodoanisole Structure

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

4'-METHOXY-[1,1'-BIPHENYL]-2-CARBONITRILE Structure

4'-METHOXY-[1,1...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

4'-METHOXY-[1,1'-BIPHENYL]-2-CARBONITRILE Structure

4'-METHOXY-[1,1...

4'-Fluoro-[1,1'-biphenyl]-2-carbonitrile Structure

4'-Fluoro-[1,1'...

~51%

9H-Fluoren-9-one,2-fluoro- Structure

9H-Fluoren-9-on...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

9H-Fluoren-9-one,1-methoxy- Structure

9H-Fluoren-9-on...

3-methoxyfluoren-9-one Structure

3-methoxyfluore...

3-Iodoanisole Structure

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

9H-Fluoren-9-one,1-methoxy- Structure

9H-Fluoren-9-on...

3-methoxyfluoren-9-one Structure

3-methoxyfluore...

4'-METHOXY-[1,1'-BIPHENYL]-2-CARBONITRILE Structure

4'-METHOXY-[1,1...

~91%

9H-Fluoren-9-one,2-methoxy- Structure

9H-Fluoren-9-on...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

9H-Fluoren-9-one,2-methoxy- Structure

9H-Fluoren-9-on...

4-Iodoanisole Structure

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

9H-Fluoren-9-one,2-methoxy- Structure

9H-Fluoren-9-on...

2'-BROMOBIPHENYL-2-CARBONITRILE Structure

2'-BROMOBIPHENY...

~57%

4-Bromo-9H-fluoren-9-one Structure

4-Bromo-9H-fluo...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

4-Bromo-9H-fluoren-9-one Structure

4-Bromo-9H-fluo...

1-Bromo-2-iodobenzene Structure

1-Bromo-2-iodob...

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

4-Bromo-9H-fluoren-9-one Structure

4-Bromo-9H-fluo...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

9H-Fluoren-9-one,1-methoxy- Structure

9H-Fluoren-9-on...

3-methoxyfluoren-9-one Structure

3-methoxyfluore...

3-Iodoanisole Structure

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

9H-Fluoren-9-one,1-methoxy- Structure

9H-Fluoren-9-on...

3-methoxyfluoren-9-one Structure

3-methoxyfluore...

1-Bromo-4-iodobenzene Structure

1-Bromo-4-iodob...

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

4'-Bromo-2-Biphenylcarbonitrile Structure

4'-Bromo-2-Biph...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

4'-Bromo-2-Biphenylcarbonitrile Structure

4'-Bromo-2-Biph...

[1,1'-biphenyl]-2-carbonitrile Structure

[1,1'-biphenyl]...

~83%

[1,1'-Biphenyl]-2-carboxamide Structure

[1,1'-Biphenyl]...

[1,1'-biphenyl]-2-carbonitrile Structure

[1,1'-biphenyl]...

~5%

9-Fluorenone Structure

[1,1'-Biphenyl]-2-carboxamide Structure

[1,1'-Biphenyl]...

Iodobenzene Structure

~%

[1,1'-Biphenyl]-2-carboxamide Structure

[1,1'-Biphenyl]...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

[1,1'-Biphenyl]-2-carboxamide Structure

[1,1'-Biphenyl]...

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

[1,1'-Biphenyl]-2-carboxamide Structure

[1,1'-Biphenyl]...

Benzonitrile Structure

~%

[1,1'-Biphenyl]-2-carboxamide Structure

[1,1'-Biphenyl]...

Iodobenzene Structure

~%

9-Fluorenone Structure

[1,1'-Biphenyl]-2-carboxamide Structure

[1,1'-Biphenyl]...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

9-Fluorenone Structure

[1,1'-Biphenyl]-2-carboxamide Structure

[1,1'-Biphenyl]...

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

9-Fluorenone Structure

[1,1'-Biphenyl]-2-carboxamide Structure

[1,1'-Biphenyl]...

Benzonitrile Structure

~%

9-Fluorenone Structure

[1,1'-Biphenyl]-2-carboxamide Structure

[1,1'-Biphenyl]...

4-Iodotoluene Structure

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

2'-METHYL-[1,1'-BIPHENYL]-2-CARBONITRILE Structure

2'-METHYL-[1,1'...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

2'-METHYL-[1,1'-BIPHENYL]-2-CARBONITRILE Structure

2'-METHYL-[1,1'...

2-naphthalen-1-ylbenzonitrile Structure

2-naphthalen-1-...

~%

BENZANTHRONE Structure

7H-Benzo[c]fluoren-7-one Structure

7H-Benzo[c]fluo...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

BENZANTHRONE Structure

7H-Benzo[c]fluoren-7-one Structure

7H-Benzo[c]fluo...

1-Iodonaphthalene Structure

1-Iodonaphthalene

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

BENZANTHRONE Structure

7H-Benzo[c]fluoren-7-one Structure

7H-Benzo[c]fluo...

1-Iodonaphthalene Structure

1-Iodonaphthalene

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

2-naphthalen-1-ylbenzonitrile Structure

2-naphthalen-1-...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

2-naphthalen-1-ylbenzonitrile Structure

2-naphthalen-1-...

2'-Fluoro-2-biphenylcarbonitrile Structure

2'-Fluoro-2-bip...

~46%

9H-Fluoren-9-one,4-fluoro- Structure

9H-Fluoren-9-on...

4-Chlorobenzonitrile Structure

4-Chlorobenzonitrile

Iodobenzene Structure

~42%

9H-Fluoren-9-one,3-chloro- Structure

9H-Fluoren-9-on...

2-(4-chlorophenyl)benzonitrile Structure

2-(4-chlorophen...

~55%

9H-Fluoren-9-one,2-chloro- Structure

9H-Fluoren-9-on...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

9H-Fluoren-9-one,2-chloro- Structure

9H-Fluoren-9-on...

1-Chloro-4-iodobenzene Structure

1-Chloro-4-iodo...

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

9H-Fluoren-9-one,2-chloro- Structure

9H-Fluoren-9-on...

1-Chloro-4-iodobenzene Structure

1-Chloro-4-iodo...

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

2-(4-chlorophenyl)benzonitrile Structure

2-(4-chlorophen...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

2-(4-chlorophenyl)benzonitrile Structure

2-(4-chlorophen...

4'-Methyl-2-cyanobiphenyl Structure

4'-Methyl-2-cya...

~89%

2-Methyl-9H-fluoren-9-one Structure

2-Methyl-9H-flu...

2-Cyanophenylboronic Acid Structure

2-Cyanophenylbo...

~%

2-Methyl-9H-fluoren-9-one Structure

2-Methyl-9H-flu...

4-Iodotoluene Structure

2-(1,3,2-Dioxaborinan-2-yl)benzonitrile Structure

2-(1,3,2-Dioxab...

~%

2-Methyl-9H-fluoren-9-one Structure

2-Methyl-9H-flu...

Iodobenzene Structure

p-Tolunitrile Structure

~60%

3-methylfluoren-9-one Structure

3-methylfluoren...

Synthesis, characterization and X-ray structures of N-hetero...

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Convenient preparation of polyfunctional aryl magnesium reag...

[Piller, Fabian M.; Appukkuttan, Prasad; Gavryushin, Andrei; Helm, Matthew; Knochel, Paul Angewandte Chemie - International Edition, 2008 , vol. 47, # 36 p. 6802 - 6806]

Radical Catalysis of Kumada Cross??Coupling Reactions Using ...

[Manolikakes, Georg; Knochel, Paul Angewandte Chemie - International Edition, 2009 , vol. 48, # 1 p. 205 - 209]

Convenient preparation of polyfunctional aryl magnesium reag...

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Microwave-assisted Negishi and Kumada cross-coupling reactio...

[Walla, Peter; Kappe, C. Oliver Chemical Communications, 2004 , # 5 p. 564 - 565]