Abstract:
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Reported herein is a photochemical strategy for
the borylation of alkyl halides using bis(catecholato)diboron as
the boron source. This method exploits the ability of a
nucleophilic dithiocarbonyl anion organocatalyst to generate
radicals via an SN2-based photochemical catalytic mechanism,
which is not reliant on the redox properties of the substrates.
Therefore, it grants access to alkyl boronic esters from readily
available but difficult-to-reduce electrophiles, including benzylic and allylic chlorides, bromides, and mesylates, which were inert to or unsuitable for previously reported metal-free borylation protocols. |