Electrochemical synthesis of nitroaromatic ketones

Iluminada Gallardo; Gonzalo Guirado; Jordi Marquet

doi:10.1002/1099-0690(20021)2002:2<261::AID-EJOC261>3.0.CO;2-6

Electrochemical synthesis of nitroaromatic ketones

Iluminada Gallardo, Gonzalo Guirado, Jordi Marquet

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

25 Citations (Scopus)

Abstract

Nitroaromatic ketones are readily prepared by nucleophilic aromatic substitution of hydrogen in nitroarenes by electrochemical oxidation. Carbanions of various ketones were added to selected nitroarenes in DMF/ketone mixtures leading to formation of the o11 complexes. The reaction was promoted using potassium feri-butoxide as a base. Useful yields were achieved (80-100%) in the C-arylation of ketones. In most cases, the process proceeded with high selectivity. This new method represents an environmentally favourable route for obtaining nitroaromatic ketones. © WILEY-VCH Verlag GmbH, 2002.

Original language	English
Pages (from-to)	261-267
Journal	European Journal of Organic Chemistry
Volume	2
Issue number	2
DOIs	https://doi.org/10.1002/1099-0690(20021)2002:2<261::AID-EJOC261>3.0.CO;2-6
Publication status	Published - 1 Jan 2002

Keywords

Electrochemistry
Ketones
Nucleophilic substitution
Oxidations

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10.1002/1099-0690(20021)2002:2<261::AID-EJOC261>3.0.CO;2-6

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abstract = "Nitroaromatic ketones are readily prepared by nucleophilic aromatic substitution of hydrogen in nitroarenes by electrochemical oxidation. Carbanions of various ketones were added to selected nitroarenes in DMF/ketone mixtures leading to formation of the o11 complexes. The reaction was promoted using potassium feri-butoxide as a base. Useful yields were achieved (80-100%) in the C-arylation of ketones. In most cases, the process proceeded with high selectivity. This new method represents an environmentally favourable route for obtaining nitroaromatic ketones. {\textcopyright} WILEY-VCH Verlag GmbH, 2002.",

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T1 - Electrochemical synthesis of nitroaromatic ketones

AU - Gallardo, Iluminada

AU - Guirado, Gonzalo

AU - Marquet, Jordi

PY - 2002/1/1

Y1 - 2002/1/1

N2 - Nitroaromatic ketones are readily prepared by nucleophilic aromatic substitution of hydrogen in nitroarenes by electrochemical oxidation. Carbanions of various ketones were added to selected nitroarenes in DMF/ketone mixtures leading to formation of the o11 complexes. The reaction was promoted using potassium feri-butoxide as a base. Useful yields were achieved (80-100%) in the C-arylation of ketones. In most cases, the process proceeded with high selectivity. This new method represents an environmentally favourable route for obtaining nitroaromatic ketones. © WILEY-VCH Verlag GmbH, 2002.

AB - Nitroaromatic ketones are readily prepared by nucleophilic aromatic substitution of hydrogen in nitroarenes by electrochemical oxidation. Carbanions of various ketones were added to selected nitroarenes in DMF/ketone mixtures leading to formation of the o11 complexes. The reaction was promoted using potassium feri-butoxide as a base. Useful yields were achieved (80-100%) in the C-arylation of ketones. In most cases, the process proceeded with high selectivity. This new method represents an environmentally favourable route for obtaining nitroaromatic ketones. © WILEY-VCH Verlag GmbH, 2002.

KW - Electrochemistry

KW - Ketones

KW - Nucleophilic substitution

KW - Oxidations

U2 - 10.1002/1099-0690(20021)2002:2<261::AID-EJOC261>3.0.CO;2-6

DO - 10.1002/1099-0690(20021)2002:2<261::AID-EJOC261>3.0.CO;2-6

M3 - Article

VL - 2

SP - 261

EP - 267

IS - 2

ER -

Electrochemical synthesis of nitroaromatic ketones

Abstract

Keywords

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