Synthesis and Application of a <i>P</i>-Chiral Phosphine Oxide N-Heterocyclic Carbene-Au(I) Catalyst
(Rp)- and (Sp)-PO-NHC-Au(I) catalysts were synthesized and used in the intramolecular hydroamination of an allene to the 2-vinyl pyrrolidine. A significant acceleration of the reaction rate was observed with these, as compared to the corresponding NHC-Au(I) catalyst. Computational studies suggested that the enhanced catalytic activity is due to the formation of a hydrogen bond between P═O and an allene terminal proton, which stabilizes the Au(I)-allene π-bond complex.
Authors
- Philip J. Karageorghis
- D. Scott Bohle (ORCID: https://orcid.org/0000-0001-5833-5696)
- Youla S. Tsantrizos (ORCID: https://orcid.org/0000-0002-6231-7498)
- Hatem M. Titi (ORCID: https://orcid.org/0000-0002-0654-1292)
- Weiwei Song (ORCID: https://orcid.org/0000-0001-5089-4127)
- Shiguang Li (ORCID: https://orcid.org/0009-0002-5558-371X)
- Rustam Z. Khaliullin (ORCID: https://orcid.org/0000-0002-9073-6753)
- Imran Kazi
- Ifenna I. Mbaezue (ORCID: https://orcid.org/0000-0002-6125-8860)
- Jiahao Zeng (ORCID: https://orcid.org/0009-0008-5381-3554)
- Daniel Chartrand (ORCID: https://orcid.org/0000-0003-0851-7701)
- Faraz Alaghemand
Institutions
- McGill University (CA)
- Université de Montréal (CA)
Publication Details
- Journal
- Organometallics
- Published
- 2025-09-16
- DOI
- https://doi.org/10.1021/acs.organomet.5c00280
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00