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.