Construction of N-Heterocyclic Systems Containing a Fully Substituted Allylic Carbon by Palladium/Phosphine Catalysis

Yohei Ogiwara*, Yui Suzuki, Kazuya Sato, Norio Sakai*

*Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, Noda, Chiba 278-8510, Japan, Email: yoheiogiwarars.tus.ac.jp, sakachemrs.noda.tus.ac.jp

Y. Ogiwara, Y. Suzuki, K. Sato, N. Sakai, Org. Lett., 2018, 20, 6965-6969.

DOI: 10.1021/acs.orglett.8b03127

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Abstract

A unique cyclization of benzamide derivatives that contain a propargyl ether by a Pd(0)/dialkyl(biaryl)phosphine catalytic system efficiently provides various six-membered N-heterocyclic compounds that contain a fully substituted carbon center. Mechanistic studies suggest that this unprecedented cyclization starts with the cleavage of a propargylic C-O bond, and a 1,3-diene has been identified as a key intermediate.

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Key Words

benzo-fused N-heterocycles

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ID: J54-Y2018