Iridium-Catalyzed Sequential Silylation and Borylation of Heteroarenes Based on Regioselective C−H Bond Activation

Masahito Murai, Naoki Nishinaka, Kazuhiko Takai

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

An iridium-catalyzed regioselective sequential silylation and borylation of heteroarenes was developed, which represents a rare example of unsymmetrical intermolecular C−H bond difunctionalization through the introduction of two different functionalities during a one-pot transformation. Although the substrate scope for the dehydrogenative silylation of heteroarenes has been limited mainly to electron-rich five-membered rings, the current reaction proceeds with both electron-rich and electron-deficient heteroarenes with the aid of heteroatom-directing C−H bond activation. The regioselectivity of the second borylation was controlled by both steric factors and the electronic effect of the silyl group installed in the first step. In combination with the classic cross-coupling reaction, this method provides rapid access to multisubstituted heteroarenes.

Original languageEnglish
Pages (from-to)5843-5847
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number20
DOIs
Publication statusPublished - May 14 2018

Keywords

  • borylation
  • C−H bond activation
  • heteroarenes
  • iridium
  • silylation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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