Cathodically activated nucleophilic aromatic substitution of hydrogen: A novel electrochemical mechanism

Iluminada Gallardo; Gonzalo Guirado; Jordi Marquet

doi:10.1039/b207168a

Cathodically activated nucleophilic aromatic substitution of hydrogen: A novel electrochemical mechanism

Iluminada Gallardo, Gonzalo Guirado, Jordi Marquet

Department of Chemistry

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

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Abstract

Cathodically activated nucleophilic aromatic substitution of hydrogen (SNArH) is reported for the first time; the 1,3,5-trinitrobenzene radical anion reacts with the nucleophile N-methylformamide leading to high yields of the σH-complex radical anion; this intermediate can be easily oxidised electrochemically by means of a three-electron mechanism giving rise to the nucleophilic aromatic substitution product (NASH product) in good yield. © 2002 The Royal Society of Chemistry.

Original language	English
Pages (from-to)	2638-2639
Journal	Chemical Communications
Volume	2
Issue number	22
DOIs	https://doi.org/10.1039/b207168a
Publication status	Published - 1 Jan 2002

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@article{b0f06966401d49d9bd2712adf8d0bff6,

title = "Cathodically activated nucleophilic aromatic substitution of hydrogen: A novel electrochemical mechanism",

abstract = "Cathodically activated nucleophilic aromatic substitution of hydrogen (SNArH) is reported for the first time; the 1,3,5-trinitrobenzene radical anion reacts with the nucleophile N-methylformamide leading to high yields of the σH-complex radical anion; this intermediate can be easily oxidised electrochemically by means of a three-electron mechanism giving rise to the nucleophilic aromatic substitution product (NASH product) in good yield. {\textcopyright} 2002 The Royal Society of Chemistry.",

author = "Iluminada Gallardo and Gonzalo Guirado and Jordi Marquet",

year = "2002",

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doi = "10.1039/b207168a",

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T1 - Cathodically activated nucleophilic aromatic substitution of hydrogen: A novel electrochemical mechanism

AU - Gallardo, Iluminada

AU - Guirado, Gonzalo

AU - Marquet, Jordi

PY - 2002/1/1

Y1 - 2002/1/1

N2 - Cathodically activated nucleophilic aromatic substitution of hydrogen (SNArH) is reported for the first time; the 1,3,5-trinitrobenzene radical anion reacts with the nucleophile N-methylformamide leading to high yields of the σH-complex radical anion; this intermediate can be easily oxidised electrochemically by means of a three-electron mechanism giving rise to the nucleophilic aromatic substitution product (NASH product) in good yield. © 2002 The Royal Society of Chemistry.

AB - Cathodically activated nucleophilic aromatic substitution of hydrogen (SNArH) is reported for the first time; the 1,3,5-trinitrobenzene radical anion reacts with the nucleophile N-methylformamide leading to high yields of the σH-complex radical anion; this intermediate can be easily oxidised electrochemically by means of a three-electron mechanism giving rise to the nucleophilic aromatic substitution product (NASH product) in good yield. © 2002 The Royal Society of Chemistry.

U2 - 10.1039/b207168a

DO - 10.1039/b207168a

M3 - Article

VL - 2

SP - 2638

EP - 2639

IS - 22

ER -

Cathodically activated nucleophilic aromatic substitution of hydrogen: A novel electrochemical mechanism

Abstract

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