Hydroboration
of alkenes is a classical reaction in organic synthesis
in which alkenes react with boranes to give alkylboranes with subsequent
oxidation resulting in alcohols. The double bond (π-bond) of
alkenes can be readily reacted with boranes owing to its high reactivity.
However, the single bond (σ-bond) of alkanes has never been
reacted. To pursue the development of σ-bond cleavage, we selected
cyclopropanes as model substrates since they present a relatively
weak σ-bond. Herein, we describe an iridium-catalyzed hydroboration
of cyclopropanes, resulting in β-methyl alkylboronates. These
unusually branched boronates can be derivatized by oxidation or cross-coupling
chemistry, accessing “designer” products that are desired
by practitioners of natural product synthesis and medicinal chemistry.
Furthermore, mechanistic investigations and theoretical studies revealed
the enabling role of the catalyst.
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