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Ring-Contraction Reaction of Substituted Tetrahydropyrans via Dehydrogenative Dual Functionalization by Nitrite-Catalyzed Double Activation of Bromine

Kazuhiro Watanabe, Tsukasa Hamada, Katsuhiko Moriyama*

*Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan, Email: moriyamafaculty.chiba-u.jp

K. Watanabe, T. Hamada, K. Moriyama, Org. Lett., 2018, 20, 5803-5807.

DOI: 10.1021/acs.orglett.8b02488 (free Supporting Information)


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Abstract

A nitrite-catalyzed ring contraction reaction of substituted tetrahydropyrans provides 2-acyltetrahydrofurans in good yields via a dehydrogenative dual functionalization under aerobic conditions. On the other hand, the oxidation reaction of 1-substituted isochromans occurred via a bromohydroxylation to give 1-(dibromoalkyl)-1-hydroxyisochromans in high yields.

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Key Words

tetrahydrofurans, oxygen


ID: J54-Y2018