Diborative Reduction of Alkynes to 1,2-Diboryl-1,2-Dimetalloalkanes: Its Application for the Synthesis of Diverse 1,2-Bis(boronate)s
- Fumiya TakahashiFumiya TakahashiDepartment of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, JapanMore by Fumiya Takahashi,
- Keisuke Nogi*Keisuke Nogi*[email protected]Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, JapanMore by Keisuke Nogi,
- Takahiro SasamoriTakahiro SasamoriGraduate School of Natural Sciences, Nagoya City University, Yamanohata 1, Mizuho-cho, Mizuho-ku, Nagoya, Aichi 467-8501, JapanMore by Takahiro Sasamori, and
- Hideki Yorimitsu*Hideki Yorimitsu*[email protected]Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, JapanMore by Hideki Yorimitsu
Abstract
Reduction of alkynes with alkali metals in the presence of B2pin2 results in diboration of alkynes. Distinct from conventional dissolving metal hydrogenations, two carbon–boron bonds and also two carbon–alkali metal bonds can be constructed in one operation to form 1,2-diboryl-1,2-dimetalloalkanes. The 1,2-diboryl-1,2-dimetalloalkanes generated are readily convertible to a wide range of vicinal bis(boronate)s. In particular, oxidation of the 1,2-dianionic species provides (E)-1,2-diborylalkenes, unique anti-selective diboration of alkynes being thus executed.
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