Triarylboranes Bearing ( <i>ortho</i> -Carboran-1-yl)aryl Groups for Catalytic Hydrogenation with Pure or Crude H <sub>2</sub>
Structural diversification of triarylboranes with unexplored substituents can expand their applications in organic synthesis. We synthesized triarylboranes that bear 2,6-F<sub>2</sub>-4-(<i>o</i>-carboran-1-yl)phenyl (Ar) groups and evaluated their Lewis acidity and catalytic activity. B(2,6-Cl<sub>2</sub>C<sub>6</sub>H<sub>3</sub>)Ar<sub>2</sub> exhibited high activity in the hydrogenation of <i>N</i>-heteroaromatics using pure (TON = up to 3960) and crude H<sub>2</sub> (TON = up to 2400). This borane also catalyzes the dehydrogenation of tetrahydroquinoline and the reductive alkylation of aliphatic amino-acid esters with H<sub>2</sub>, demonstrating the first catalytic applications of carboranyl-substituted triarylboranes in diverse molecular transformations.
Authors
- Anil Chauhan
- Yusei Hisata (ORCID: https://orcid.org/0009-0006-4192-368X)
- Yoichi Hoshimoto
- Riku Ikeda
Institutions
- Institute for Schools of the Future (US)
- Graduate School USA (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-12-26
- DOI
- https://doi.org/10.1021/acs.orglett.5c04669
- Citations
- 1
- Primary Topic
- Boron Compounds in Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.36