New rigid polycyclic bis(phosphane) for asymmetric catalysis
Authors:
- K. Michał Pietrusiewicz,
- Katarzyna Szwaczko,
- Barbara Mirosław,
- Izabela Dybała,
- Radomir Jasiński,
- Oleg M. Demchuk
Abstract
A simple, highly efficient synthesis of a series of novel chiral non-racemic rigid tetracyclic phosphorus ligands, applicable in important chemical asymmetric transformations, was performed. In a tandem cross-coupling/C-H bond activation reaction, a well-recognised and readily available ligand (R,R)-NORPHOS was used as the starting material. The palladium complexes of new ligands were obtained and characterised on the example of a crystalline dichloropalladium complex of [(1R,2R,9S,10S,11R,12R)-4-phenyltetracyclo[8.2.1.02,9.03,8]trideca-3,5,7-triene-11,12-diyl]bis(diphenylphosphane). A notably high activity and stereoselectivity of the palladium catalysts based on the new ligands were confirmed in a model asymmetric allylic substitution reaction. Herein, we discuss the geometry of the palladium complexes formed and its impact on the efficiency of the catalysts. A comparison of their geometric features with other bis(phosphane) ligand complexes found in the Cambridge Structural Database and built density functional theory (DFT) commutated models is also presented and rationalised.
- Record ID
- CUT517caa06599747fc8dfc66bf7d5ace80
- Publication categories
- ;
- Author
- Journal series
- Molecules, ISSN , e-ISSN 1420-3049, Biweekly
- Issue year
- 2019
- Vol
- 24
- No
- 3
- Pages
- [1-22]
- Other elements of collation
- rys.; schem.; tab.; Bibliografia (na s.) - 20-22; Bibliografia (liczba pozycji) - 43; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 24, Iss. 3
- Keywords in English
- bis(phosphane) palladium complex, metallacycle, NORPHOS, allylic alkylation, asymmetric catalysis, chiral phosphines, C-H bond activation, polycyclic compounds, stereoselective synthesis, DFT calculations
- DOI
- DOI:10.3390/molecules24030571 Opening in a new tab
- URL
- https://www.mdpi.com/1420-3049/24/3/571 Opening in a new tab
- Language
- eng (en) English
- License
- Score (nominal)
- 140
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT517caa06599747fc8dfc66bf7d5ace80/
- URN
urn:pkr-prod:CUT517caa06599747fc8dfc66bf7d5ace80
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.