Mild and Efficient Method for Decarboxylative Bromination of α,β-Unsaturated Carboxylic Acids with Dess-Martin Periodinane

Abstract

A simple and mild method for decarboxylative bromination of α,β-unsaturated carboxylic acids has been developed using Dess-Martin Periodinane (DMP) in combination with tetraethylammonium bromide (TEAB) at room temperature. High yields of the corresponding bromoalkenes were obtained.

Dess-Martin periodinane - tetraethylammonium bromide - decaboxylation - bromoalkenes

References

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14

General experimental procedure: To a stirred suspension of DMP (1.1 equiv) in anhyd CH₂Cl₂ (15 mL) was added TEAB (1.1 equiv) in one portion. The resultant mixture was stirred r.t. for 5 min followed by addition of α,β-unsaturated carboxylic acid (1.0 equiv) and stirring was continued at r.t. until the starting material had been completely consumed (TLC). The reaction mixture was diluted with CH₂Cl₂ and washed successively with 10% aq sodium bisulfite solution (2 × 15 mL), 10% NaHCO₃ (2 × 15 mL), H₂O (1 × 10 mL), and brine (1 × 10 mL). The organic layer was dried over Na₂SO₄ and concentrated in vacuo. The residue obtained was purified by silica gel column chromatography (10% EtOAc-hexane) to afford pure bromoalkenes.