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

Czégéni, Csilla Enikő and Fekete, Mariann and Tóbiás, Eszter and Udvardy, Antal and Győrváriné Horváth, Henrietta and Papp, Gábor Csaba and Joó, Ferenc (2020) Redox Isomerization of Allylic Alcohols Catalyzed by New Water-Soluble Rh(I)-N-Heterocyclic Carbene Complexes. CATALYSTS, 10 (11). ISSN 2073-4344

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Abstract

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.

Item Type: Article
Additional Information: Funding Agency and Grant Number: European Regional Development FundEuropean Union (EU) [GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00004]; Thematic Excellence Programme of the Ministry for Innovation and Technology of Hungary of the University of Debrecen [ED_18-1-2019-0028]; Hungarian National Research, Development and Innovation Office [FK-128333]; EUEuropean Union (EU) Funding text: The research was supported by the EU and co-financed by the European Regional Development Fund (under the projects GINOP-2.3.2-15-2016-00008 and GINOP-2.3.3-15-2016-00004), and by the Thematic Excellence Programme of the Ministry for Innovation and Technology of Hungary (ED_18-1-2019-0028), within the framework of the Vehicle Industry thematic programme of the University of Debrecen. The financial support of the Hungarian National Research, Development and Innovation Office (FK-128333) is greatly acknowledged. MTA-DE Redox and Homogeneous Catalytic Reaction Mechanisms Research Group, P.O. Box 400, Debrecen, H-4002, Hungary Department of Physical Chemistry, University of Debrecen, P.O. Box 400, Debrecen, H-4002, Hungary Export Date: 6 February 2021 Correspondence Address: Czégéni, C.E.; MTA-DE Redox and Homogeneous Catalytic Reaction Mechanisms Research Group, P.O. Box 400, Hungary; email: nagy.csilla@science.unideb.hu Funding details: European Commission, EC Funding details: Debreceni Egyetem, DE Funding details: National Research, Development and Innovation Office, FK-128333 Funding details: ED_18-1-2019-0028 Funding details: European Regional Development Fund, FEDER, GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00004 Funding text 1: Funding: The research was supported by the EU and co-financed by the European Regional Development Fund (under the projects GINOP-2.3.2-15-2016-00008 and GINOP-2.3.3-15-2016-00004), and by the Thematic Excellence Programme of the Ministry for Innovation and Technology of Hungary (ED_18-1-2019-0028), within the framework of the Vehicle Industry thematic programme of the University of Debrecen. The financial support of the Hungarian National Research, Development and Innovation Office (FK-128333) is greatly acknowledged.
Subjects: Q Science / természettudomány > QD Chemistry / kémia
SWORD Depositor: MTMT SWORD
Depositing User: MTMT SWORD
Date Deposited: 08 Mar 2021 11:49
Last Modified: 08 Mar 2021 11:49
URI: http://real.mtak.hu/id/eprint/122009

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