Synthesis of a Helical Phosphine and a Catalytic Study of Its Palladium Complex

0522979 - ÚCHP 2021 RIV US eng J - Journal Article
Beránek, Tomáš - Žádný, Jaroslav - Strašák, Tomáš - Karban, Jindřich - Císařová, I. - Sýkora, Jan - Storch, Jan
Synthesis of a Helical Phosphine and a Catalytic Study of Its Palladium Complex.
ACS Omega. Roč. 5, č. 1 (2020), s. 882-892. ISSN 2470-1343. E-ISSN 2470-1343
R&D Projects: GA TA ČR TA04010082
Institutional support: RVO:67985858
Keywords : stereoselective syntheses * asymmetric-synthesis * azahelicenes
OECD category: Organic chemistry
Impact factor: 3.512, year: 2020
Method of publishing: Open access
https://pubs.acs.org/doi/pdf/10.1021/acsomega.9b03830

In this study, 9-(diphenylphosphanyl)[7]helicene was prepared as a suitable ligand for the subsequent synthesis of palladium complexes. The corresponding PdL2Cl2 complex was then successfully obtained in both racemic and enantiopure forms. The PdL2Cl2 complex emerges exclusively in the trans arrangement showing dynamic interconversion between its homo-and heterochiral forms as evidenced by 31P NMR. The trans arrangement was ultimately confirmed by X-ray crystallography using single crystals of the homochiral complex. Additionally, the PdL2Cl2 complex was subjected to screening of its catalytic activity in a Suzuki-type reaction of aryl bromides with aryl boronic acids showing fair yields of the resulting biaryls. However, the final asymmetric reactions catalyzed by the optically pure PdL2Cl2 complex provided targeted binaphtyls only in negligible enantiomeric excess.
Permanent Link: http://hdl.handle.net/11104/0307388