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Further Information

Vilsmeier-Haack Reaction

The Vilsmeier Reaction allows the formylation of electron-rich arenes.

Mechanism of the Vilsmeier-Haak Reaction

The formylating agent, also known as the Vilsmeyer-Haack Reagent, is formed in situ from DMF and phosphorus oxychlorid:

An electrophilic aromatic substitution leads to α-chloro amines, which are rapidly hydrolyzed during work up to give the aldehyde:

Recent Literature

An Efficient Route to 1-Vinylpyrrole-2-carbaldehydes
A. I. Mikhaleva, A. V. Ivanoc, E. V. Skital'tseva, I. A. Ushakov, A. M. Vasil'tsov, B. A. Trofimov, Synthesis, 2009, 587-590.

Metal-Free One-Pot Conversion of Electron-Rich Aromatics into Aromatic Nitriles
S. Ushijima, H. Togo, Synlett, 2010, 1067-1070.

Synthesis of 4-Ynamides and Cyclization by the Vilsmeier Reagent to Dihydrofuran-2(3H)-ones
J. Zheng, J.-H. Lin, L.-Y. Yu, Y. Wei, X. Zheng, J.-C. Xiao, Org. Lett., 2015, 17, 6126-6129.

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N,N-Dimethylformamide
Y.-R. Zhu, J.-H. Lin, J.-C. Xiao, Synlett, 2022, 33, 259-263.