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Diborative Reduction of Alkynes to 1,2-Diboryl-1,2-Dimetalloalkanes: Its Application for the Synthesis of Diverse 1,2-Bis(boronate)s

Author:
Takahashi, Fumiya, Nogi, Keisuke, Sasamori, Takahiro, Yorimitsu, Hideki
Source:
Organic letters 2019 v.21 no.12 pp. 4739-4744
ISSN:
1523-7052
Subject:
alkali metals, alkynes, boronic acids, chemical structure, oxidation
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.
Agid:
6478210