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Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

By Masahito Murai (1359642), Naoki Nishinaka (6611174), Mizuki Kimura (1453261) and Kazuhiko Takai (1359651)


Despite 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

Topics: Biophysics, Biochemistry, Cell Biology, Neuroscience, Biotechnology, Cancer, Mental Health, Environmental Sciences not elsewhere classified, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, building blocks, presence, Regioselective Functionalization, cleavable, bromination, 9- silafluorenes, building block, utility, regioselectivity, Bromination, Nitration, functionalization, method, synthesis, nitration, 9- silafluorene-containing π-, material, molecule, Borylation, electron-rich position, Dimethyl, bromo groups, borylation, unsymmetrically, 2- methoxy -9-silafluorene, iridium-catalyzed, bond
Year: 2019
DOI identifier: 10.1021/acs.joc.9b00598.s002
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Provided by: FigShare
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