Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO

Srimanta Manna; Sandipan Jana; Tapish Saboo; Arun Maji; Debabrata Maiti

doi:10.1039/c3cc41576g

Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO

Srimanta Manna, Sandipan Jana, Tapish Saboo, Arun Maji, Debabrata Maiti

Pharmaceutical Sciences

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

144 Scopus citations

Abstract

Nitroolefins are usually synthesized using the Henry reaction. Here we report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from α,β-unsaturated carboxylic acids using t-butylnitrite (t-BuONO) and TEMPO. α,β-Unsaturated carboxylic acids bearing β-aromatic and β-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.

Original language	English
Pages (from-to)	5286-5288
Number of pages	3
Journal	Chemical Communications
Volume	49
Issue number	46
DOIs	https://doi.org/10.1039/c3cc41576g
State	Published - May 14 2013

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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abstract = "Nitroolefins are usually synthesized using the Henry reaction. Here we report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from α,β-unsaturated carboxylic acids using t-butylnitrite (t-BuONO) and TEMPO. α,β-Unsaturated carboxylic acids bearing β-aromatic and β-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.",

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AU - Saboo, Tapish

AU - Maji, Arun

AU - Maiti, Debabrata

PY - 2013/5/14

Y1 - 2013/5/14

N2 - Nitroolefins are usually synthesized using the Henry reaction. Here we report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from α,β-unsaturated carboxylic acids using t-butylnitrite (t-BuONO) and TEMPO. α,β-Unsaturated carboxylic acids bearing β-aromatic and β-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.

AB - Nitroolefins are usually synthesized using the Henry reaction. Here we report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from α,β-unsaturated carboxylic acids using t-butylnitrite (t-BuONO) and TEMPO. α,β-Unsaturated carboxylic acids bearing β-aromatic and β-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.

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Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO

Abstract

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