A photocatalytic acid- and base-free Meerwein-Ponndorf-Verley-type reduction using a [Ru(bpy)<inf>3</inf>]<sup>2+</sup>/viologen couple

Jose Raul Herance; Belén Ferrer; Jose Luis Bourdelande; Jordi Marquet; Hermenegildo Garcia

doi:10.1002/chem.200501365

A photocatalytic acid- and base-free Meerwein-Ponndorf-Verley-type reduction using a [Ru(bpy)<inf>3</inf>]<sup>2+</sup>/viologen couple

Jose Raul Herance, Belén Ferrer, Jose Luis Bourdelande, Jordi Marquet, Hermenegildo Garcia

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

23 Citations (Scopus)

Abstract

A photocatalytic system to effect the Meerwein-Ponndorf-Verley reduction of carbonylic compounds to alcohols has been developed. The system comprises [Ru(bpy)3]2+ as a photosensitizer, triethanolamine as a sacrificial electron donor, viologen as an electron acceptor, and the carbonyl compound and iPrOH as Meerwein-Ponndorf-Verley reagents. The photocatalytic reaction can be performed in neat iPrOH or in l-butyl-3-methylimidazolium ionic liquid. Mass spectrometric detection of the viologen hydride derivative VH + confirms that this species is the reducing agent responsible for the carbonyl compound reduction. The reaction intermediates involved in the photocatalytic system have also been characterized by laser flash photolysis. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

Original language	English
Pages (from-to)	3890-3895
Journal	Chemistry - A European Journal
Volume	12
Issue number	14
DOIs	https://doi.org/10.1002/chem.200501365
Publication status	Published - 3 May 2006

Keywords

Ionic liquids
Meerwein-Ponndorf-Verley reduction
NADH
Photocatalysis
Ruthenium

Access to Document

10.1002/chem.200501365

Cite this

@article{79e2b9e61efc437e8424de42913e21d2,

title = "A photocatalytic acid- and base-free Meerwein-Ponndorf-Verley-type reduction using a [Ru(bpy)3]2+/viologen couple",

abstract = "A photocatalytic system to effect the Meerwein-Ponndorf-Verley reduction of carbonylic compounds to alcohols has been developed. The system comprises [Ru(bpy)3]2+ as a photosensitizer, triethanolamine as a sacrificial electron donor, viologen as an electron acceptor, and the carbonyl compound and iPrOH as Meerwein-Ponndorf-Verley reagents. The photocatalytic reaction can be performed in neat iPrOH or in l-butyl-3-methylimidazolium ionic liquid. Mass spectrometric detection of the viologen hydride derivative VH + confirms that this species is the reducing agent responsible for the carbonyl compound reduction. The reaction intermediates involved in the photocatalytic system have also been characterized by laser flash photolysis. {\textcopyright} 2006 Wiley-VCH Verlag GmbH & Co. KGaA.",

keywords = "Ionic liquids, Meerwein-Ponndorf-Verley reduction, NADH, Photocatalysis, Ruthenium",

author = "Herance, {Jose Raul} and Bel{\'e}n Ferrer and Bourdelande, {Jose Luis} and Jordi Marquet and Hermenegildo Garcia",

year = "2006",

month = may,

day = "3",

doi = "10.1002/chem.200501365",

language = "English",

volume = "12",

pages = "3890--3895",

number = "14",

}

TY - JOUR

T1 - A photocatalytic acid- and base-free Meerwein-Ponndorf-Verley-type reduction using a [Ru(bpy)3]2+/viologen couple

AU - Herance, Jose Raul

AU - Ferrer, Belén

AU - Bourdelande, Jose Luis

AU - Marquet, Jordi

AU - Garcia, Hermenegildo

PY - 2006/5/3

Y1 - 2006/5/3

N2 - A photocatalytic system to effect the Meerwein-Ponndorf-Verley reduction of carbonylic compounds to alcohols has been developed. The system comprises [Ru(bpy)3]2+ as a photosensitizer, triethanolamine as a sacrificial electron donor, viologen as an electron acceptor, and the carbonyl compound and iPrOH as Meerwein-Ponndorf-Verley reagents. The photocatalytic reaction can be performed in neat iPrOH or in l-butyl-3-methylimidazolium ionic liquid. Mass spectrometric detection of the viologen hydride derivative VH + confirms that this species is the reducing agent responsible for the carbonyl compound reduction. The reaction intermediates involved in the photocatalytic system have also been characterized by laser flash photolysis. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

AB - A photocatalytic system to effect the Meerwein-Ponndorf-Verley reduction of carbonylic compounds to alcohols has been developed. The system comprises [Ru(bpy)3]2+ as a photosensitizer, triethanolamine as a sacrificial electron donor, viologen as an electron acceptor, and the carbonyl compound and iPrOH as Meerwein-Ponndorf-Verley reagents. The photocatalytic reaction can be performed in neat iPrOH or in l-butyl-3-methylimidazolium ionic liquid. Mass spectrometric detection of the viologen hydride derivative VH + confirms that this species is the reducing agent responsible for the carbonyl compound reduction. The reaction intermediates involved in the photocatalytic system have also been characterized by laser flash photolysis. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

KW - Ionic liquids

KW - Meerwein-Ponndorf-Verley reduction

KW - NADH

KW - Photocatalysis

KW - Ruthenium

U2 - 10.1002/chem.200501365

DO - 10.1002/chem.200501365

M3 - Article

VL - 12

SP - 3890

EP - 3895

IS - 14

ER -

A photocatalytic acid- and base-free Meerwein-Ponndorf-Verley-type reduction using a [Ru(bpy)<inf>3</inf>]<sup>2+</sup>/viologen couple

Abstract

Keywords

Access to Document

Fingerprint

Cite this