Enantiopure <i>P</i>-Chiral Secondary Phosphines (P*HRR′) from the Catalytic Asymmetric Hydrogenation of P═C Bonds
We report the first bottleable enantiopure <i>P</i>-chiral secondary phosphines from the rhodium-catalyzed asymmetric hydrogenation of phosphaalkenes. Catalytic asymmetric hydrogenation, a reaction of broad academic and industrial importance for C═C, N═C, and O═C bonds, has not previously been reported for the P═C bond. The hydrogenation of ArP═CR<sub>2</sub> (Ar = Mes, <i>m</i>-Xyl and TMOP; R = Ph, 4-C<sub>6</sub>H<sub>4</sub>F) affords four unprecedented <i>P</i>-stereogenic secondary phosphines in 76%-90% isolated yields with 91%-97% enantiomeric excess (ee). These isolable <i>P</i>-chiral secondary phosphines are configurationally stable indefinitely in the solid state and show only modest loss in ee when kept in solution for over a month at room temperature.
Authors
- Michael D. Fryzuk (ORCID: https://orcid.org/0000-0002-3844-098X)
- Derek P. Gates (ORCID: https://orcid.org/0000-0002-0025-0486)
- Brian O. Patrick (ORCID: https://orcid.org/0000-0002-2921-8439)
- Tian Zhang (ORCID: https://orcid.org/0000-0003-3840-4839)
- Ming Li
- Aaron A. Mitchell
Institutions
- University of British Columbia (CA)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2024-09-13
- DOI
- https://doi.org/10.1021/jacs.4c09501
- Citations
- 7
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.11
Funders
- Natural Sciences and Engineering Research Council of Canada