Alkylation of nitroaromatics with trialkylborane

Anna Shifman; Namasivayam Palani; Shmaryahu Hoz

doi:10.1002/(SICI)1521-3773(20000303)39:5<944::AID-ANIE944>3.0.CO;2-I

Alkylation of nitroaromatics with trialkylborane

Anna Shifman, Namasivayam Palani, Shmaryahu Hoz

Department of Chemistry

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

16 Scopus citations

Abstract

A novel, facile, aromatic substitution reaction of nitroaromatics is described. When p-dinitrobenzene (1) is treated with trialkylborane in the presence of potassium tert-butoxide, it furnishes p-alkylnitrobenzene (2) in high yield. A tentative mechanism is suggested involving alkyl radicals and radical anions of the nitroaromatic substrate.

Original language	English
Pages (from-to)	944-945
Number of pages	2
Journal	Angewandte Chemie - International Edition
Volume	39
Issue number	5
DOIs	https://doi.org/10.1002/(SICI)1521-3773(20000303)39:5<944::AID-ANIE944>3.0.CO;2-I
State	Published - 3 Mar 2000

Keywords

Alkylations
Aromatic substitutions
Boron
Synthetic methods

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10.1002/(SICI)1521-3773(20000303)39:5<944::AID-ANIE944>3.0.CO;2-I

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AU - Hoz, Shmaryahu

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N2 - A novel, facile, aromatic substitution reaction of nitroaromatics is described. When p-dinitrobenzene (1) is treated with trialkylborane in the presence of potassium tert-butoxide, it furnishes p-alkylnitrobenzene (2) in high yield. A tentative mechanism is suggested involving alkyl radicals and radical anions of the nitroaromatic substrate.

AB - A novel, facile, aromatic substitution reaction of nitroaromatics is described. When p-dinitrobenzene (1) is treated with trialkylborane in the presence of potassium tert-butoxide, it furnishes p-alkylnitrobenzene (2) in high yield. A tentative mechanism is suggested involving alkyl radicals and radical anions of the nitroaromatic substrate.

KW - Alkylations

KW - Aromatic substitutions

KW - Boron

KW - Synthetic methods

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Alkylation of nitroaromatics with trialkylborane

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