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A Photocatalytic Acid‐ and Base‐Free Meerwein–Ponndorf–Verley‐Type Reduction Using a [Ru(bpy) 3 ] 2+ /Viologen Couple
Author(s) -
Herance Jose Raul,
Ferrer Belén,
Bourdelande Jose Luis,
Marquet Jordi,
Garcia Hermenegildo
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501365
Subject(s) - chemistry , photocatalysis , viologen , photochemistry , triethanolamine , flash photolysis , reagent , electron acceptor , electron donor , photosensitizer , medicinal chemistry , catalysis , organic chemistry , reaction rate constant , kinetics , analytical chemistry (journal) , physics , quantum mechanics
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 i PrOH as Meerwein–Ponndorf–Verley reagents. The photocatalytic reaction can be performed in neat i PrOH 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.