Reductive Difunctionalization of Aryl Alkenes with Sodium Metal and Reduction-Resistant Alkoxy-Substituted Electrophiles

Mizuki Fukazawa, Fumiya Takahashi, Keisuke Nogi*, Takahiro Sasamori and Hideki Yorimitsu*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan, Email: knogikuchem.kyoto-u.ac.jp, yorikuchem.kyoto-u.ac.jp

M. Fukazawa, F. Takahashi, K. Nogi, T. Sasamori, H. Yorimitsu, Org. Lett., 2020, 22, 2303-2307.

DOI: 10.1021/acs.orglett.0c00490

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Abstract

Alkali metals promote a general reductive 1,2-diborations and 1,2-dicarbofunctionalizations of alkenes by employing trimethoxyborane and strained cyclic ethers such as oxirane and oxetane. In addition, unsymmetrical carbo- or thioborations have been accomplished via treatment with trimethoxyborane followed by carbon or sulfur electrophiles.

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Key Words

diboronates, benzylboronates, sodium

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ID: J54-Y2020