Synthesis of Heavy Fluorous Ruthenium Metathesis Catalysts Using the Stereoselective Addition of Polyfluoroalkyllithium to Sterically Hindered Diimines

0446525 - ÚOCHB 2016 RIV US eng J - Článek v odborném periodiku
Hošek, J. - Rybáčková, M. - Čejka, J. - Cvačka, Josef - Kvíčala, J.
Synthesis of Heavy Fluorous Ruthenium Metathesis Catalysts Using the Stereoselective Addition of Polyfluoroalkyllithium to Sterically Hindered Diimines.
Organometallics. Roč. 34, č. 13 (2015), s. 3327-3334. ISSN 0276-7333. E-ISSN 1520-6041
Institucionální podpora: RVO:61388963
Klíčová slova: ring-closing metathesis * form tetrasubstituted olefins * N-heterocyclic carbene
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 4.186, rok: 2015

The stereoselective addition of 2-(perfluorohexyl)ethyllithium to moderately hindered diimines led to racemic diamines, which were further transformed to light or heavy fluorous analogues of Hoveyda-Grubbs second-generation precatalysts. The complex bearing the NHC ligand modified with four polyfluoroalkyl ponytails represents the first known example of an alkene metathesis precatalyst retaining its heavy fluorous properties in the active catalytic form. The synthesized complexes match the activity and stability of a commercial Hoveyda-Grubbs second-generation precatalyst in model RCM reactions forming iii- and tetrasubstituted double bonds. The fluorophilic catalyst was successfully recycled using heavy fluorous separation techniques.
Trvalý link: http://hdl.handle.net/11104/0248523