Asymmetric Construction of a SeCF<sub>3</sub>-Substituted Stereocenter by CuH-Catalyzed Hydroboration of 1-SeCF<sub>3</sub>-Alkenes
A copper hydride (CuH)-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylseleno (SeCF<sub>3</sub>)-alkenes with H-Bpin has been developed. The regio- and enantioselective hydrocupration of an <i>in situ</i> generated CuH species is followed by a boration reaction to successfully construct a SeCF<sub>3</sub>- and Bpin-substituted chiral carbon center. The key to success is the appropriate choice of <i>t</i>Bu-modified biphosphine ligands, which enables an overwhelming high reaction efficiency.
Authors
- Kosuke Yasui (ORCID: https://orcid.org/0000-0002-3906-8307)
- Yuki Kojima (ORCID: https://orcid.org/0000-0002-3756-223X)
- Koji Hirano (ORCID: https://orcid.org/0000-0001-9752-1985)
- Yuji Nishii (ORCID: https://orcid.org/0000-0002-6824-0639)
- Haruka Matsui
Institutions
- Center for Research and Interdisciplinarity (FR)
- Graduate School USA (US)
- The University of Osaka (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-20
- DOI
- https://doi.org/10.1021/acs.orglett.5c00330
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Hoansha Foundation
- Japan Society for the Promotion of Science
- Fusion Oriented REsearch for disruptive Science and Technology