Visible-Light-Driven Silylation of C(sp <sup>2</sup> )–O Bonds with Silylboranes via Nickel Catalysis
Developing a general and efficient method for C(sp<sup>2</sup>)-O bond silylation that tolerates broad silyl groups under mild conditions remains a key challenge. Here, we report that naphthol and phenol derivatives bearing -OPO<sub>3</sub><sup><i>t</i></sup>Bu<sub>2</sub> and -OC(O)N<sup><i>i</i></sup>Pr<sub>2</sub> leaving groups undergo silylation with silylboranes using a Ni(0) catalyst with no added ligand via C-O bond cleavage. Blue LED irradiation markedly accelerates the reaction, broadening the applicable silyl groups under ambient conditions.
Authors
- Itsuki Nohira
- Ken Tanaka (ORCID: https://orcid.org/0000-0003-0534-7559)
- Yuki Nagashima (ORCID: https://orcid.org/0000-0001-8470-5638)
- Shiho Ishigaki
- Satoshi Yamazaki (ORCID: https://orcid.org/0000-0002-0624-8416)
Institutions
- Tokyo Institute of Technology (JP)
- Shanghai Institute for Science of Science (CN)
- Institute of Science Tokyo (JP)
- The University of Tokyo (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-11-10
- DOI
- https://doi.org/10.1021/acs.orglett.5c03986
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00