Development of an organosilica material containing ordered triene coordination sites and its application in borylation of aryl iodides
An organosilica material containing conjugated triene moieties (triene-SiO2-TMS; TMS = trimethylsilyl) was developed. The structure of triene-SiO2-TMS was characterized by nitrogen adsorption, X-ray diffraction (XRD), and transmission electron microscopy (TEM) to reveal that triene-SiO2-TMS consists of organosilica particles with a molecular-scale ordered arrangement of conjugated triene moieties on the surface. Treatment of triene-SiO2-TMS with commercially available Pd(dba)<sub>2</sub> in THF at ambient temperature afforded Pd-triene-SiO2-TMS, in which Pd was immobilized on the surface. Pd-triene-SiO2-TMS exhibited catalytic activity towards the borylation of aryl iodides with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin). The reactions proceeded without the addition of exogenous ligands such as phosphines. The catalyst exhibited good functional group compatibility including electron-withdrawing and -donating functional groups. The recyclability of Pd-triene-SiO2-TMS was examined to demonstrate its moderate reusability.
Authors
- Yuki Inagaki (ORCID: https://orcid.org/0000-0002-6681-386X)
- Yoshihiro Shimoyama (ORCID: https://orcid.org/0000-0003-3728-9381)
- Shinji Inagaki (ORCID: https://orcid.org/0000-0003-0405-5511)
- Masaru Yoshida (ORCID: https://orcid.org/0000-0002-9220-4312)
- Yumiko Nakajima (ORCID: https://orcid.org/0000-0001-6813-8733)
- Hajime Kawanami (ORCID: https://orcid.org/0000-0002-2679-2662)
- Shinji Tanaka (ORCID: https://orcid.org/0000-0003-2002-5582)
Institutions
- Tokyo Institute of Technology (JP)
- University of Tsukuba (JP)
- National Institute of Advanced Industrial Science and Technology (JP)
Publication Details
- Journal
- Dalton Transactions
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5dt02087e
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00