Palladium-Catalyzed Dearomative Methoxyallylation of 3-Nitroindoles with Allyl Carbonates.

Herein we report a Pd-catalyzed dearomative methoxyallylation of 3-nitroindoles with readily available allyl carbonates. Good yields (up to 86 %) and diastereoselectivity (up to >20:1 dr) are obtained for a wide range of substrates. The compatibility of gram-scale synthesis and the relatively low catalyst loading (down to 1 mol % of [Pd]) enhance the practicality of this method. The kinetic experiments indicate that the rate-determining step of this reaction is the nucleophilic attack of the alkoxide anion.