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

Masahito Murai, Naoki Nishinaka, Mizuki Kimura, Kazuhiko Takai

Research output: Contribution to journalArticle

Abstract

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 ?-conjugated molecules.

Original languageEnglish
Pages (from-to)5667-5676
Number of pages10
JournalJournal of Organic Chemistry
Volume84
Issue number9
DOIs
Publication statusPublished - May 3 2019

ASJC Scopus subject areas

  • Organic Chemistry

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