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)(...

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Published inCatalysts Vol. 10; no. 11; p. 1361
Main Authors Czégéni, Csilla Enikő, Fekete, Marianna, Tóbiás, Eszter, Udvardy, Antal, Horváth, Henrietta, Papp, Gábor, Joó, Ferenc
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.11.2020
Subjects
Alcohol
Alcohols
Aqueous solutions
Carbon
Catalysts
Catalytic activity
Chemical reactions
Hydrogenation
Isomerization
Ketones
Ligands
Phosphines
Rhodium
Selectivity
Sodium
Solvents
Substrates
Water chemistry
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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