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Visible-light-enabled denitrative carboxylation of β-nitrostyrenes: a direct photocatalytic approach to cinnamic acids†
Shubhangi Tripathi,Lal Dhar S. Yadav
New Journal of Chemistry Pub Date : 01/26/2018 00:00:00 , DOI:10.1039/C7NJ04578F
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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