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Open AccessArticle

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

1
MTA-DE Redox and Homogeneous Catalytic Reaction Mechanisms Research Group, P.O. Box 400, H-4002 Debrecen, Hungary
2
Department of Physical Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary
*
Author to whom correspondence should be addressed.
Catalysts 2020, 10(11), 1361; https://doi.org/10.3390/catal10111361
Received: 8 November 2020 / Revised: 19 November 2020 / Accepted: 20 November 2020 / Published: 23 November 2020
(This article belongs to the Special Issue Catalysis in Heterocyclic and Organometallic Synthesis)
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. View Full-Text
Keywords: allylic alcohols; redox isomerization; N-heterocyclic carbenes; rhodium; water soluble; homogeneous catalysis allylic alcohols; redox isomerization; N-heterocyclic carbenes; rhodium; water soluble; homogeneous catalysis
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MDPI and ACS Style

Czégéni, C.E.; Fekete, M.; Tóbiás, E.; Udvardy, A.; Horváth, H.; Papp, G.; Joó, F. Redox Isomerization of Allylic Alcohols Catalyzed by New Water-Soluble Rh(I)-N-Heterocyclic Carbene Complexes. Catalysts 2020, 10, 1361.

AMA Style

Czégéni CE, Fekete M, Tóbiás E, Udvardy A, Horváth H, Papp G, Joó F. Redox Isomerization of Allylic Alcohols Catalyzed by New Water-Soluble Rh(I)-N-Heterocyclic Carbene Complexes. Catalysts. 2020; 10(11):1361.

Chicago/Turabian Style

Czégéni, Csilla E.; Fekete, Marianna; Tóbiás, Eszter; Udvardy, Antal; Horváth, Henrietta; Papp, Gábor; Joó, Ferenc. 2020. "Redox Isomerization of Allylic Alcohols Catalyzed by New Water-Soluble Rh(I)-N-Heterocyclic Carbene Complexes" Catalysts 10, no. 11: 1361.

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