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Bromoallenes as Synthetic Equivalents of Allyl Dications: Synthesis of Medium-Sized Nitrogen Heterocycles through the Cyclization of Bromoallenes in the Presence of a Palladium(0) Catalyst and an Alcohol

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  • We thank Prof. Dr. M. Mori, Hokkaido University, for useful information regarding the mechanism of the reaction. This work was supported by a Grant-in-Aid for Encouragement of Young Scientists from the Ministry of Education, Science, Sports, and Culture of Japan. H.H. is grateful for a Research Fellowship for Young Scientists from the Japan Society for the Promotion of Science (JSPS).

Abstract

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A highly regio- and stereoselective synthesis of medium-sized nitrogen heterocycles has been developed (see scheme), based on the discovery that bromoallenes can act as an allyl dication equivalent in the presence of a palladium(0) catalyst and an alcohol. The intramolecular nucleophilic attack takes place exclusively at the central carbon atom of the allene moiety.

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