figshare
Browse
jo9b00598_si_002.cif (34.25 kB)

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

Download (34.25 kB)
dataset
posted on 2019-04-02, 00:00 authored by Masahito Murai, Naoki Nishinaka, Mizuki Kimura, Kazuhiko Takai
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.

History