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2.5.7.4 Formylation with N-Methylaniline and a Transition-Metal Catalyst

DOI: 10.1055/sos-SD-213-00191

Zhang, N.; Dong, D.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (20142336.

Traditional formylation of organic compounds is accomplished by the Vilsmeier, Reimer–Tiemann, Rieche, or Duff reactions, which generally require heating at elevated temperature, and treatment with excess base or acid during workup. Occasionally, the reaction conditions required for these methods are not compatible with a particular functional group. As a novel formylation method, the ruthenium-catalyzed oxidative coupling of free indoles with N-methylaniline offers a new pathway to easily introduce the formyl functionality (Scheme 4).[‌11‌] The formylation occurs exclusively at the 3-position of indole.

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