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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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Supplementary files

Article information


Submitted
19 Jan 2015
Accepted
20 Feb 2015
First published
24 Feb 2015

Dalton Trans., 2015,44, 13007-13016
Article type
Paper
Author version available

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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