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2.6.1.1.2.3 Indium-Mediated Synthesis of -Aryl-Substituted Homoallylic Amines

DOI: 10.1055/sos-SD-211-00177

Xi, C.; Chen, C.Science of Synthesis: Multicomponent Reactions, (20142444.

Ethyl vinyl ether (16) is used as an aldehyde equivalent for the generation of imines in the indium-mediated one-pot reaction of aromatic amines 17 with allyl bromide (9), which affords N-aryl-substituted homoallylic amines 18 (Scheme 5).[‌12‌] No aromatic allylamine is obtained and ethyl vinyl ether is the best choice of ether in this reaction. Anilines can tolerate halo, alkyl, or electron-donating alkoxy groups as substituents, to give the corresponding amine products in high yield. However, when an electron-deficient aromatic amine is used, only a small amount of the desired product is obtained.

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