Synthesis and Application of Robust Spiro [Fluorene-9] CAAC Ruthenium Alkylidene Complexes for the "One-Pot" Conversion of Allyl Acetate to Butane-1,4-diol.

Autor: Erdélyi Á; Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, 1117, Hungary.; Research Centre for Biochemical, Environmental and Chemical Engineering, Department of MOL Hydrocarbon and Coal Processing, University of Pannonia, Egyetem u. 10, Veszprém, 8210, Hungary., Farkas V; Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, 1117, Hungary.; Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, Budapest, 1111, Hungary., Turczel G; Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, 1117, Hungary., Nagyházi M; Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, 1117, Hungary.; Research Centre for Biochemical, Environmental and Chemical Engineering, Department of MOL Hydrocarbon and Coal Processing, University of Pannonia, Egyetem u. 10, Veszprém, 8210, Hungary., Bényei A; Department of Physical Chemistry, Faculty of Science and Technology, University of Debrecen, Egyetem tér 1, Debrecen, 4032, Hungary., Recta MLL; Department of Physical Chemistry, Faculty of Science and Technology, University of Debrecen, Egyetem tér 1, Debrecen, 4032, Hungary., Nagy T; Department of Applied Chemistry, Faculty of Science and Technology, University of Debrecen, Egyetem tér 1, Debrecen, 4032, Hungary., Kéki S; Department of Applied Chemistry, Faculty of Science and Technology, University of Debrecen, Egyetem tér 1, Debrecen, 4032, Hungary., Osterthun O; Institut für Technische und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 2, 52074, Aachen, Germany., Klankermayer J; Institut für Technische und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 2, 52074, Aachen, Germany., Tuba R; Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, 1117, Hungary.; Research Centre for Biochemical, Environmental and Chemical Engineering, Department of MOL Hydrocarbon and Coal Processing, University of Pannonia, Egyetem u. 10, Veszprém, 8210, Hungary.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Sep 02; Vol. 30 (49), pp. e202401918. Date of Electronic Publication: 2024 Aug 02.
DOI: 10.1002/chem.202401918
Abstrakt: A series of a novel CAAC ligands featuring a spiro-fluorene group have been synthesized and complexed with ruthenium alkylidenes, yielding the corresponding Hoveyda-type derivatives as a new family of olefin metathesis catalysts. The novel complexes have been characterized by XRD, HRMS and NMR measurements. The synthetised complexes were tested in catalysis and showed good activity in olefin metathesis, as demonstrated on diethyl diallylmalonate and allyl acetate substrates. The unique backbone in the ligand with the large, yet inflexible condensed system renders interesting properties to the catalyst, exemplified by the good catalytic performance and improved Z-selectivity. In addition, the complex can also serve as a hydrogenation catalyst in a consecutive (one-pot) reaction. The latter reaction can convert allyl acetate to butane-1,4-diol, a valuable chemical intermediate for biodegradable polybutylene succinate (PBS).
(© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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