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Issue 39, 2013
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Synthesis of substituted nitroolefins: a copper catalyzed nitrodecarboxylation of unsaturated carboxylic acids

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Abstract

A novel, mild and convenient method for the nitrodecarboxylation of substituted cinnamic acid derivatives to their nitroolefins is achieved using a catalytic amount of CuCl (10 mol%) and tert-butyl nitrite (2 equiv.) as a nitrating agent in the presence of air. This reaction provides a useful method for the synthesis of β,β-disubstituted nitroolefin derivatives, which are generally difficult to access from other conventional methods. Additionally, this reaction is selective as the E-isomer of the acid derivatives furnishes the corresponding E-nitroolefins. One more salient feature of the method is, unlike other methods, no metal nitrates or HNO3 are employed for the transformation.

Graphical abstract: Synthesis of substituted nitroolefins: a copper catalyzed nitrodecarboxylation of unsaturated carboxylic acids

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Supplementary files

Article information


Submitted
09 Jul 2013
Accepted
16 Aug 2013
First published
19 Aug 2013

Org. Biomol. Chem., 2013,11, 6713-6716
Article type
Communication

Synthesis of substituted nitroolefins: a copper catalyzed nitrodecarboxylation of unsaturated carboxylic acids

B. V. Rokade and K. R. Prabhu, Org. Biomol. Chem., 2013, 11, 6713 DOI: 10.1039/C3OB41408F

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