Redox Isomerization of Allylic Alcohols Catalyzed by New Water-Soluble Rh(I)-N-Heterocyclic Carbene Complexes

New water-soluble, N-heterocyclic carbene (NHC) or mixed NHC/tertiary phosphine complexes [RhCl(cod)(sSIMes)], Na2[Rh(bmim)(cod)(mtppts)], and [Rh(bmim)(cod)(pta)]BF4 were synthetized and applied for the first time as catalysts in redox isomerization of allylic alcohols in aqueous media. [RhCl(cod)(...

Full description

Saved in:
Bibliographic Details
Published in:Catalysts 2020-11, Vol.10 (11), p.1361
Main Authors: Czégéni, Csilla Enikő, Fekete, Marianna, Tóbiás, Eszter, Udvardy, Antal, Horváth, Henrietta, Papp, Gábor, Joó, Ferenc
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Aqueous solutions
Carbon
Catalysts
Catalytic activity
Chemical reactions
Hydrogenation
Isomerization
Ketones
Ligands
Phosphines
Rhodium
Selectivity
Sodium
Solvents
Substrates
Water chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:New water-soluble, N-heterocyclic carbene (NHC) or mixed NHC/tertiary phosphine complexes [RhCl(cod)(sSIMes)], Na2[Rh(bmim)(cod)(mtppts)], and [Rh(bmim)(cod)(pta)]BF4 were synthetized and applied for the first time as catalysts in redox isomerization of allylic alcohols in aqueous media. [RhCl(cod)(sSIMes)] (with added sulfonated triphenylphosphine) and [Rh(bmim)(cod)(pta)]BF4 catalyzed selectively the transformation of allylic alcohols to the corresponding ketones. The highest catalytic activity, TOF = 152 h−1 (TOF = (mol reacted substrate) × (mol catalyst × time)−1) was observed in redox isomerization of hept-1-en-3-ol ([S]/[cat] = 100). The catalysts were reused in the aqueous phase at least three times, with only modest loss of the catalytic activity and selectivity.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal10111361