jo9b00598_si_002.cif (34.25 kB)
Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration
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posted on 2019-04-02, 00:00 authored by Masahito Murai, Naoki Nishinaka, Mizuki Kimura, Kazuhiko TakaiDespite
the utility of 9-silafluorenes as functional materials
and as building blocks, methods for efficient functionalization of
their backbone are rare, probably because of the presence of easily
cleavable C–Si bonds. Although controlling the regioselectivity
of iridium-catalyzed direct borylation of C–H bonds is difficult,
we found that bromination and nitration of 2-methoxy-9-silafluorene
under mild conditions occurred predominantly at the electron-rich
position. The resulting product having methoxy and bromo groups can
be utilized as a building block for the synthesis of unsymmetrically
substituted 9-silafluorene-containing π-conjugated molecules.
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building blockspresenceRegioselective Functionalizationcleavablebromination9- silafluorenesbuilding blockutilityregioselectivityBrominationNitrationfunctionalizationmethodsynthesisnitration9- silafluorene-containing π-materialmoleculeBorylationelectron-rich positionDimethylbromo groupsborylationunsymmetrically2- methoxy -9-silafluoreneiridium-catalyzedbond
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