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Issue 29, 2015
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Iridium–bipyridine periodic mesoporous organosilica catalyzed direct C–H borylation using a pinacolborane

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Abstract

Heterogeneous catalysis for direct C–H borylation of arenes and heteroarenes in the combination of iridium (Ir) complex fixed on periodic mesoporous organosilica containing bipyridine ligands within the framework (Ir-BPy-PMO) and pinacolborane (HBpin) is reported. Ir-BPy-PMO showed higher catalytic activity toward the borylation of benzene with inexpensive HBpin compared to expensive bis(pinacolato)diboron (B2pin2). The precatalyst could be handled without the use of a glove box. The catalyst was easily recovered from reaction mixtures by simple filtration under air. The recovered catalyst still showed good catalytic activity for at least three more times for the borylation of benzene. A variety of arenes and heteroarenes were successfully borylated with high boron efficiency by Ir-BPy-PMO using HBpin, whereas almost no activity was observed for borylation of some heteroarenes with B2pin2. The system using Ir-BPy-PMO and HBpin was also utilized in syntheses of multi-boronated thiophene-based building blocks containing ladder-, acenefused-, and fused-thiophene skeletons. The combination of a stable and reusable solid catalyst and inexpensive HBpin is expected to be superior to conventional approaches for the development of industrial applications.

Graphical abstract: Iridium–bipyridine periodic mesoporous organosilica catalyzed direct C–H borylation using a pinacolborane

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Publication details

The article was received on 19 Jan 2015, accepted on 20 Feb 2015 and first published on 24 Feb 2015


Article type: Paper
DOI: 10.1039/C5DT00239G
Citation: Dalton Trans., 2015,44, 13007-13016
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    Iridium–bipyridine periodic mesoporous organosilica catalyzed direct C–H borylation using a pinacolborane

    Y. Maegawa and S. Inagaki, Dalton Trans., 2015, 44, 13007
    DOI: 10.1039/C5DT00239G

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