Fe(III)/Pyridine-Mediated Decarboxylative Nitration of α,β-Unsaturated Acids with Iron Nitrate

Abstract

A novel and efficient method for the synthesis of (E)-nitroolefins in moderate to excellent yields is developed by Fe(III)/pyridine-mediated decarboxylative nitration of α,β-unsaturated acids with iron nitrate. A series of α,β-unsaturated acids are well tolerated in this procedure.

Key words

nitroolefins - decarboxylative - nitration - α,β-unsaturated acids - iron nitrate

• References and Notes

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• 14 Procedure for the Synthesis of β-Nitrostyrene The mixture of cinnamic acid (0.5 mmol), Fe(NO₃)₃ (1.0 mmol), pyridine (0.5 mmol), and toluene (2 mL) was stirred at 100 °C for 12 h. After cooling to r.t., the reaction mixture was washed with H₂O (10 mL) and extracted by EtOAc (3×). The organic phase was dried with anhydrous MgSO₄. The mixture was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (15% EtOAc–n-hexane) to afford pure product. Yellow solid (90%, 77 mg). ¹H NMR (400 MHz, CDCl₃): δ = 7.37–7.57 (m, 5 H), 7.59 (d, J = 13.7 Hz, 1 H), 8.01 (d, J = 13.7 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ =129.16, 129.43, 130.14, 132.15, 137.19, 139.06.