A Photocatalytic Acid- and Base-Free Meerwein-Ponndorf-Verley-Type Reduction Using a [Ru(bpy)3]2+/Viologen Couple

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 iP...

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Bibliographic Details
Published in:Chemistry : a European journal 2006-05, Vol.12 (14), p.3890-3895
Main Authors: Herance, Jose Raul, Ferrer, Belén, Bourdelande, Jose Luis, Marquet, Jordi, Garcia, Hermenegildo
Format: Article
Language:English
Subjects:
ionic liquids
Meerwein-Ponndorf-Verley reduction
NADH
photocatalysis
ruthenium
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Summary: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 1‐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. Similar to the natural NADH/NAD+ enzymatic factor of biological carbonyl reductions, a photocatalytic system (see scheme, TEOA=triethanolamine) to effect the Meerwein–Ponndorf–Verley reduction of carbonylic compounds in iPrOH and 1‐butyl‐3‐methylimidazolium ionic liquid has been developed.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200501365