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Issue 5, 2018
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Visible-light-enabled denitrative carboxylation of β-nitrostyrenes: a direct photocatalytic approach to cinnamic acids

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Abstract

The first workable application of β-nitrostyrenes and CBr4 as coupling partners for a highly stereoselective synthesis of (E)-cinnamic acids under visible light photoredox catalysis is reported. The reaction involves a radical denitrative tribromomethylation/hydrolysis cascade to afford (E)-cinnamic acids in excellent yields at room temperature in a one-pot procedure. Moreover, the implementation of visible light as a clean and inexpensive energy source and CBr4 as the latent source of carboxylic groups makes the protocol reconcilable with the present day scenario of organic synthesis.

Graphical abstract: Visible-light-enabled denitrative carboxylation of β-nitrostyrenes: a direct photocatalytic approach to cinnamic acids

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Publication details

The article was received on 23 Nov 2017, accepted on 25 Jan 2018 and first published on 26 Jan 2018


Article type: Paper
DOI: 10.1039/C7NJ04578F
Citation: New J. Chem., 2018,42, 3765-3769
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    Visible-light-enabled denitrative carboxylation of β-nitrostyrenes: a direct photocatalytic approach to cinnamic acids

    S. Tripathi and L. D. S. Yadav, New J. Chem., 2018, 42, 3765
    DOI: 10.1039/C7NJ04578F

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