A Modular Approach to Atropisomeric Bisphosphines of Diversified Electronic Density on Phosphorus Atoms
Oleg M. Demchuk,
Aleksandra Martyna,
Mateusz Kwaśnik,
Katarzyna Szwaczko,
Dorota Strzelecka,
Barbara Mirosław,
Kazimierz Michał Pietrusiewicz,
Zofia Urbanczyk-Lipkowska
Affiliations
Oleg M. Demchuk
Institute of Biological Sciences, Faculty of Science and Health, The John Paul II Catholic University of Lublin, Konstantynów 1J/4.03, 20-708 Lublin, Poland
Aleksandra Martyna
Institute of Biological Sciences, Faculty of Science and Health, The John Paul II Catholic University of Lublin, Konstantynów 1J/4.03, 20-708 Lublin, Poland
Mateusz Kwaśnik
Institute of Biological Sciences, Faculty of Science and Health, The John Paul II Catholic University of Lublin, Konstantynów 1J/4.03, 20-708 Lublin, Poland
Katarzyna Szwaczko
Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, Gliniana 33, 20-031 Lublin, Poland
Dorota Strzelecka
Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, Gliniana 33, 20-031 Lublin, Poland
Barbara Mirosław
Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, Gliniana 33, 20-031 Lublin, Poland
Kazimierz Michał Pietrusiewicz
Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, Gliniana 33, 20-031 Lublin, Poland
Zofia Urbanczyk-Lipkowska
Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
The series of C2-symmetric biaryl core-based non-racemic bisphosphines possessing substituents of different electronic properties: both EDG and EWG were obtained in a short sequence of good yielding transformations, started from commercial 1,3-dimethyl-2-nitrobenzene. Several different approaches leading to the desirable ligands were practically evaluated. Notably, the synthesis of the entire series of ligands could be performed with the utilization of a single early-stage precursor DIDAB (6,6′-diiodo-2,2′,4,4′-tetramethylbiphenyl-3,3′-diamine), which could be easily obtained in enantiomerically pure form. The obtained compounds at concentrations of 50 and 200 µM showed various biological activity against normal human dermal fibroblast, ranging from inactivity through time-dependent action and ending up with high toxicity.
